{"id":"https://openalex.org/W2732405764","doi":"https://doi.org/10.1021/jacs.7b05277","title":"Intramolecular Crossed [2+2] Photocycloaddition through Visible Light-Induced Energy Transfer","display_name":"Intramolecular Crossed [2+2] Photocycloaddition through Visible Light-Induced Energy Transfer","publication_year":2017,"publication_date":"2017-07-06","ids":{"openalex":"https://openalex.org/W2732405764","doi":"https://doi.org/10.1021/jacs.7b05277","mag":"2732405764","pmid":"https://pubmed.ncbi.nlm.nih.gov/28683547"},"language":"en","primary_location":{"id":"doi:10.1021/jacs.7b05277","doi":"https://doi.org/10.1021/jacs.7b05277","is_oa":false,"landing_page_url":"https://doi.org/10.1021/jacs.7b05277","pdf_url":null,"source":{"id":"https://openalex.org/S111155417","display_name":"Journal of the American Chemical Society","issn_l":"0002-7863","issn":["0002-7863","1520-5126","1943-2984"],"is_oa":false,"is_in_doaj":false,"is_core":true,"listed_in":["cwts-core","dongbi-a","jufo-3","ki-jl-3","medline","norway-2","poland-200","russia-white-list-1","vabb-shw"],"host_organization":"https://openalex.org/P4310320006","host_organization_name":"American Chemical Society","host_organization_lineage":["https://openalex.org/P4310320006"],"host_organization_lineage_names":["American Chemical Society"],"type":"journal"},"license":null,"license_id":null,"version":"publishedVersion","is_accepted":true,"is_published":true,"raw_source_name":"Journal of the American Chemical Society","raw_type":"journal-article"},"volume":null,"type":"article","indexed_in":["crossref","pubmed"],"open_access":{"is_oa":false,"oa_status":"closed","oa_url":null,"any_repository_has_fulltext":false},"authorships":[{"author_position":"first","author":{"id":"https://openalex.org/A5017502914","display_name":"Jiannan Zhao","orcid":"https://orcid.org/0000-0002-5546-7383","observed_orcids":["https://orcid.org/0000-0002-5546-7383"]},"institutions":[{"id":"https://openalex.org/I161318765","display_name":"University of California, Los Angeles","ror":"https://ror.org/046rm7j60","country_code":"US","type":"education","lineage":["https://openalex.org/I161318765"]}],"countries":["US"],"is_corresponding":false,"raw_author_name":"Jiannan Zhao","raw_affiliation_strings":["Department of Chemistry and\rBiochemistry, University of California, Los Angeles, Los Angeles, California 90095-1569, United States"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Department of Chemistry and\rBiochemistry, University of California, Los Angeles, Los Angeles, California 90095-1569, United States","institution_ids":["https://openalex.org/I161318765"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5074358313","display_name":"Jonathan L. Brosmer","orcid":"https://orcid.org/0000-0001-7218-8397","observed_orcids":["https://orcid.org/0000-0001-7218-8397"]},"institutions":[{"id":"https://openalex.org/I161318765","display_name":"University of California, Los Angeles","ror":"https://ror.org/046rm7j60","country_code":"US","type":"education","lineage":["https://openalex.org/I161318765"]}],"countries":["US"],"is_corresponding":false,"raw_author_name":"Jonathan L. Brosmer","raw_affiliation_strings":["Department of Chemistry and\rBiochemistry, University of California, Los Angeles, Los Angeles, California 90095-1569, United States"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Department of Chemistry and\rBiochemistry, University of California, Los Angeles, Los Angeles, California 90095-1569, United States","institution_ids":["https://openalex.org/I161318765"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5026393426","display_name":"Qingxuan Tang","orcid":null,"observed_orcids":[]},"institutions":[{"id":"https://openalex.org/I161318765","display_name":"University of California, Los Angeles","ror":"https://ror.org/046rm7j60","country_code":"US","type":"education","lineage":["https://openalex.org/I161318765"]}],"countries":["US"],"is_corresponding":false,"raw_author_name":"Qingxuan Tang","raw_affiliation_strings":["Department of Chemistry and\rBiochemistry, University of California, Los Angeles, Los Angeles, California 90095-1569, United States"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Department of Chemistry and\rBiochemistry, University of California, Los Angeles, Los Angeles, California 90095-1569, United States","institution_ids":["https://openalex.org/I161318765"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5055785990","display_name":"Zhongyue John Yang","orcid":"https://orcid.org/0000-0003-0395-6617","observed_orcids":["https://orcid.org/0000-0003-0395-6617"]},"institutions":[{"id":"https://openalex.org/I161318765","display_name":"University of California, Los Angeles","ror":"https://ror.org/046rm7j60","country_code":"US","type":"education","lineage":["https://openalex.org/I161318765"]}],"countries":["US"],"is_corresponding":false,"raw_author_name":"Zhongyue Yang","raw_affiliation_strings":["Department of Chemistry and\rBiochemistry, University of California, Los Angeles, Los Angeles, California 90095-1569, United States"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Department of Chemistry and\rBiochemistry, University of California, Los Angeles, Los Angeles, California 90095-1569, United States","institution_ids":["https://openalex.org/I161318765"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5042178740","display_name":"Kendall N. Houk","orcid":"https://orcid.org/0000-0002-8387-5261","observed_orcids":["https://orcid.org/0000-0002-8387-5261"]},"institutions":[{"id":"https://openalex.org/I161318765","display_name":"University of California, Los Angeles","ror":"https://ror.org/046rm7j60","country_code":"US","type":"education","lineage":["https://openalex.org/I161318765"]}],"countries":["US"],"is_corresponding":false,"raw_author_name":"K. N. Houk","raw_affiliation_strings":["Department of Chemistry and\rBiochemistry, University of California, Los Angeles, Los Angeles, California 90095-1569, United States"],"raw_orcid":"https://orcid.org/0000-0002-8387-5261","affiliations":[{"raw_affiliation_string":"Department of Chemistry and\rBiochemistry, University of California, Los Angeles, Los Angeles, California 90095-1569, United States","institution_ids":["https://openalex.org/I161318765"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5029282916","display_name":"Paula L. Diaconescu","orcid":"https://orcid.org/0000-0003-2732-4155","observed_orcids":["https://orcid.org/0000-0003-2732-4155"]},"institutions":[{"id":"https://openalex.org/I161318765","display_name":"University of California, Los Angeles","ror":"https://ror.org/046rm7j60","country_code":"US","type":"education","lineage":["https://openalex.org/I161318765"]}],"countries":["US"],"is_corresponding":false,"raw_author_name":"Paula L. Diaconescu","raw_affiliation_strings":["Department of Chemistry and\rBiochemistry, University of California, Los Angeles, Los Angeles, California 90095-1569, United States"],"raw_orcid":"https://orcid.org/0000-0003-2732-4155","affiliations":[{"raw_affiliation_string":"Department of Chemistry and\rBiochemistry, University of California, Los Angeles, Los Angeles, California 90095-1569, United States","institution_ids":["https://openalex.org/I161318765"]}]},{"author_position":"last","author":{"id":"https://openalex.org/A5039075754","display_name":"Ohyun Kwon","orcid":"https://orcid.org/0000-0002-5405-3971","observed_orcids":["https://orcid.org/0000-0002-5405-3971"]},"institutions":[{"id":"https://openalex.org/I161318765","display_name":"University of California, Los Angeles","ror":"https://ror.org/046rm7j60","country_code":"US","type":"education","lineage":["https://openalex.org/I161318765"]}],"countries":["US"],"is_corresponding":true,"raw_author_name":"Ohyun Kwon","raw_affiliation_strings":["Department of Chemistry and\rBiochemistry, University of California, Los Angeles, Los Angeles, California 90095-1569, United States"],"raw_orcid":"https://orcid.org/0000-0002-5405-3971","affiliations":[{"raw_affiliation_string":"Department of Chemistry and\rBiochemistry, University of California, Los Angeles, Los Angeles, California 90095-1569, United States","institution_ids":["https://openalex.org/I161318765"]}]}],"institutions":[],"countries_distinct_count":1,"institutions_distinct_count":1,"corresponding_author_ids":["https://openalex.org/A5039075754"],"corresponding_institution_ids":["https://openalex.org/I161318765"],"apc_list":{"value":4500,"currency":"USD","value_usd":4500},"apc_paid":null,"fwci":6.9609,"has_fulltext":false,"cited_by_count":150,"citation_normalized_percentile":{"value":0.98343917,"is_in_top_1_percent":false,"is_in_top_10_percent":true},"cited_by_percentile_year":{"min":98,"max":100},"biblio":{"volume":"139","issue":"29","first_page":"9807","last_page":"9810"},"is_retracted":false,"is_paratext":false,"is_xpac":false,"primary_topic":{"id":"https://openalex.org/T10701","display_name":"Radical Photochemical Reactions","score":0.8604000210762024,"subfield":{"id":"https://openalex.org/subfields/1605","display_name":"Organic Chemistry"},"field":{"id":"https://openalex.org/fields/16","display_name":"Chemistry"},"domain":{"id":"https://openalex.org/domains/3","display_name":"Physical Sciences"}},"topics":[{"id":"https://openalex.org/T10701","display_name":"Radical Photochemical Reactions","score":0.8604000210762024,"subfield":{"id":"https://openalex.org/subfields/1605","display_name":"Organic Chemistry"},"field":{"id":"https://openalex.org/fields/16","display_name":"Chemistry"},"domain":{"id":"https://openalex.org/domains/3","display_name":"Physical Sciences"}},{"id":"https://openalex.org/T12893","display_name":"Organic Chemistry Cycloaddition Reactions","score":0.06310000270605087,"subfield":{"id":"https://openalex.org/subfields/1605","display_name":"Organic Chemistry"},"field":{"id":"https://openalex.org/fields/16","display_name":"Chemistry"},"domain":{"id":"https://openalex.org/domains/3","display_name":"Physical Sciences"}},{"id":"https://openalex.org/T10871","display_name":"Catalytic Alkyne Reactions","score":0.0210999995470047,"subfield":{"id":"https://openalex.org/subfields/1605","display_name":"Organic Chemistry"},"field":{"id":"https://openalex.org/fields/16","display_name":"Chemistry"},"domain":{"id":"https://openalex.org/domains/3","display_name":"Physical Sciences"}}],"keywords":[{"id":"https://openalex.org/keywords/intramolecular-2-2-photocycloaddition","display_name":"intramolecular [2+2] photocycloaddition","score":0.9190000295639038},{"id":"https://openalex.org/keywords/dienones","display_name":"dienones","score":0.8029999732971191},{"id":"https://openalex.org/keywords/visible-light-sensitization","display_name":"visible light sensitization","score":0.5849999785423279},{"id":"https://openalex.org/keywords/triplet-energy-transfer","display_name":"triplet energy transfer","score":0.968999981880188},{"id":"https://openalex.org/keywords/regioselectivity","display_name":"regioselectivity","score":0.9819999933242798},{"id":"https://openalex.org/keywords/photocatalysis","display_name":"photocatalysis","score":0.5640000104904175}],"concepts":[{"id":"https://openalex.org/C185592680","wikidata":"https://www.wikidata.org/wiki/Q2329","display_name":"Chemistry","level":0,"score":0.9667351841926575},{"id":"https://openalex.org/C75079739","wikidata":"https://www.wikidata.org/wiki/Q1571801","display_name":"Intramolecular force","level":2,"score":0.9023897647857666},{"id":"https://openalex.org/C2911029807","wikidata":"https://www.wikidata.org/wiki/Q80232","display_name":"Cyclobutanes","level":4,"score":0.8489396572113037},{"id":"https://openalex.org/C59759590","wikidata":"https://www.wikidata.org/wiki/Q2275927","display_name":"Regioselectivity","level":3,"score":0.8488837480545044},{"id":"https://openalex.org/C2779664164","wikidata":"https://www.wikidata.org/wiki/Q898648","display_name":"Cycloaddition","level":3,"score":0.6232019662857056},{"id":"https://openalex.org/C528581852","wikidata":"https://www.wikidata.org/wiki/Q877","display_name":"Iridium","level":3,"score":0.6224530339241028},{"id":"https://openalex.org/C75473681","wikidata":"https://www.wikidata.org/wiki/Q188651","display_name":"Photochemistry","level":1,"score":0.6051101088523865},{"id":"https://openalex.org/C106447425","wikidata":"https://www.wikidata.org/wiki/Q11379","display_name":"Energy transfer","level":2,"score":0.5996955633163452},{"id":"https://openalex.org/C104663316","wikidata":"https://www.wikidata.org/wiki/Q76299","display_name":"Visible spectrum","level":2,"score":0.5516241788864136},{"id":"https://openalex.org/C161790260","wikidata":"https://www.wikidata.org/wiki/Q82264","display_name":"Catalysis","level":2,"score":0.48355767130851746},{"id":"https://openalex.org/C172456720","wikidata":"https://www.wikidata.org/wiki/Q2945392","display_name":"Intramolecular reaction","level":3,"score":0.42656487226486206},{"id":"https://openalex.org/C52859227","wikidata":"https://www.wikidata.org/wiki/Q7877","display_name":"Electrochemistry","level":3,"score":0.42285510897636414},{"id":"https://openalex.org/C71240020","wikidata":"https://www.wikidata.org/wiki/Q186011","display_name":"Stereochemistry","level":1,"score":0.29188066720962524},{"id":"https://openalex.org/C178790620","wikidata":"https://www.wikidata.org/wiki/Q11351","display_name":"Organic chemistry","level":1,"score":0.13712775707244873},{"id":"https://openalex.org/C147789679","wikidata":"https://www.wikidata.org/wiki/Q11372","display_name":"Physical chemistry","level":1,"score":0.11156076192855835},{"id":"https://openalex.org/C17525397","wikidata":"https://www.wikidata.org/wiki/Q176140","display_name":"Electrode","level":2,"score":0.0},{"id":"https://openalex.org/C41999313","wikidata":"https://www.wikidata.org/wiki/Q489328","display_name":"Molecular physics","level":1,"score":0.0},{"id":"https://openalex.org/C121332964","wikidata":"https://www.wikidata.org/wiki/Q413","display_name":"Physics","level":0,"score":0.0},{"id":"https://openalex.org/C49040817","wikidata":"https://www.wikidata.org/wiki/Q193091","display_name":"Optoelectronics","level":1,"score":0.0}],"mesh":[{"descriptor_ui":"D002384","descriptor_name":"Catalysis","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D003503","descriptor_name":"Cyclobutanes","qualifier_ui":"Q000138","qualifier_name":"chemical synthesis","is_major_topic":true},{"descriptor_ui":"D003503","descriptor_name":"Cyclobutanes","qualifier_ui":"Q000737","qualifier_name":"chemistry","is_major_topic":false},{"descriptor_ui":"D004735","descriptor_name":"Energy Transfer","qualifier_ui":"Q000528","qualifier_name":"radiation effects","is_major_topic":true},{"descriptor_ui":"D007495","descriptor_name":"Iridium","qualifier_ui":"Q000737","qualifier_name":"chemistry","is_major_topic":false},{"descriptor_ui":"D007659","descriptor_name":"Ketones","qualifier_ui":"Q000737","qualifier_name":"chemistry","is_major_topic":true},{"descriptor_ui":"D008027","descriptor_name":"Light","qualifier_ui":null,"qualifier_name":null,"is_major_topic":true},{"descriptor_ui":"D015394","descriptor_name":"Molecular Structure","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D055668","descriptor_name":"Photochemical Processes","qualifier_ui":null,"qualifier_name":null,"is_major_topic":true},{"descriptor_ui":"D061565","descriptor_name":"Cycloaddition Reaction","qualifier_ui":null,"qualifier_name":null,"is_major_topic":true}],"locations_count":2,"locations":[{"id":"doi:10.1021/jacs.7b05277","doi":"https://doi.org/10.1021/jacs.7b05277","is_oa":false,"landing_page_url":"https://doi.org/10.1021/jacs.7b05277","pdf_url":null,"source":{"id":"https://openalex.org/S111155417","display_name":"Journal of the American Chemical Society","issn_l":"0002-7863","issn":["0002-7863","1520-5126","1943-2984"],"is_oa":false,"is_in_doaj":false,"is_core":true,"listed_in":["cwts-core","dongbi-a","jufo-3","ki-jl-3","medline","norway-2","poland-200","russia-white-list-1","vabb-shw"],"host_organization":"https://openalex.org/P4310320006","host_organization_name":"American Chemical Society","host_organization_lineage":["https://openalex.org/P4310320006"],"host_organization_lineage_names":["American Chemical Society"],"type":"journal"},"license":null,"license_id":null,"version":"publishedVersion","is_accepted":true,"is_published":true,"raw_source_name":"Journal of the American Chemical Society","raw_type":"journal-article"},{"id":"pmid:28683547","doi":null,"is_oa":false,"landing_page_url":"https://pubmed.ncbi.nlm.nih.gov/28683547","pdf_url":null,"source":{"id":"https://openalex.org/S4306525036","display_name":"PubMed","issn_l":null,"issn":null,"is_oa":false,"is_in_doaj":false,"is_core":false,"listed_in":[],"host_organization":"https://openalex.org/I1299303238","host_organization_name":"National Institutes of Health","host_organization_lineage":["https://openalex.org/I1299303238"],"host_organization_lineage_names":[],"type":"repository"},"license":null,"license_id":null,"version":"publishedVersion","is_accepted":true,"is_published":true,"raw_source_name":"Journal of the American Chemical Society","raw_type":"Journal Article"}],"best_oa_location":null,"sustainable_development_goals":[],"study_designs":[],"awards":[{"id":"https://openalex.org/G1315798237","display_name":null,"funder_award_id":"GM 071779","funder_id":"https://openalex.org/F4320337354","funder_display_name":"National Institute of General Medical Sciences"},{"id":"https://openalex.org/G1455760090","display_name":null,"funder_award_id":"CHE- 1361104","funder_id":"https://openalex.org/F4320337393","funder_display_name":"Division of Chemistry"},{"id":"https://openalex.org/G4321583944","display_name":null,"funder_award_id":"CHE-1362999","funder_id":"https://openalex.org/F4320337393","funder_display_name":"Division of Chemistry"}],"funders":[{"id":"https://openalex.org/F4320337354","display_name":"National Institute of General Medical Sciences","ror":"https://ror.org/04q48ey07"},{"id":"https://openalex.org/F4320337393","display_name":"Division of Chemistry","ror":"https://ror.org/01ar8dr59"}],"has_content":{"grobid_xml":false,"pdf":false},"content_urls":null,"referenced_works_count":62,"referenced_works":["https://openalex.org/W1759459935","https://openalex.org/W1764586463","https://openalex.org/W1801273252","https://openalex.org/W1970393749","https://openalex.org/W1974366166","https://openalex.org/W1979445286","https://openalex.org/W1982032801","https://openalex.org/W1990793155","https://openalex.org/W1996941025","https://openalex.org/W2001316067","https://openalex.org/W2004493861","https://openalex.org/W2020317621","https://openalex.org/W2023606237","https://openalex.org/W2025515577","https://openalex.org/W2026837389","https://openalex.org/W2029539013","https://openalex.org/W2039318684","https://openalex.org/W2041452153","https://openalex.org/W2045033152","https://openalex.org/W2046759784","https://openalex.org/W2061470694","https://openalex.org/W2063510590","https://openalex.org/W2063874456","https://openalex.org/W2066541770","https://openalex.org/W2072195331","https://openalex.org/W2075176849","https://openalex.org/W2077436655","https://openalex.org/W2078244474","https://openalex.org/W2084239999","https://openalex.org/W2092708809","https://openalex.org/W2093174332","https://openalex.org/W2094129737","https://openalex.org/W2106473549","https://openalex.org/W2110413027","https://openalex.org/W2115973550","https://openalex.org/W2128463776","https://openalex.org/W2132659080","https://openalex.org/W2137963327","https://openalex.org/W2146410562","https://openalex.org/W2148284364","https://openalex.org/W2189447191","https://openalex.org/W2321120636","https://openalex.org/W2323375596","https://openalex.org/W2325194817","https://openalex.org/W2331283941","https://openalex.org/W2342441681","https://openalex.org/W2433923815","https://openalex.org/W2464470593","https://openalex.org/W2491458126","https://openalex.org/W2507620840","https://openalex.org/W2518378475","https://openalex.org/W2561089820","https://openalex.org/W2564444771","https://openalex.org/W2949155689","https://openalex.org/W2949528699","https://openalex.org/W2950439198","https://openalex.org/W2950545306","https://openalex.org/W2952400515","https://openalex.org/W2953387790","https://openalex.org/W3004600253","https://openalex.org/W4211252082","https://openalex.org/W4285719527"],"related_works":["https://openalex.org/W4406353580","https://openalex.org/W4396817005","https://openalex.org/W3134282954","https://openalex.org/W2029253088","https://openalex.org/W2092708809","https://openalex.org/W2097670082","https://openalex.org/W3033155948","https://openalex.org/W7204493155","https://openalex.org/W4309682003","https://openalex.org/W4255529757"],"abstract_inverted_index":{"Herein,":[0],"we":[1],"present":[2],"the":[3,82,90],"intramolecular":[4],"[2+2]":[5,28],"cycloadditions":[6],"of":[7,26,64,73,84],"dienones":[8],"promoted":[9],"through":[10],"sensitization,":[11],"using":[12],"a":[13],"polypyridyl":[14],"iridium(III)":[15],"catalyst,":[16],"to":[17,23,55,61,70],"form":[18],"bridged":[19,45],"cyclobutanes.":[20],"In":[21],"contrast":[22],"previous":[24,62],"examples":[25],"straight":[27],"cycloadditions,":[29],"these":[30],"efficient":[31],"crossed":[32],"additions":[33],"were":[34],"achieved":[35],"under":[36],"irradiation":[37],"with":[38,48],"visible":[39],"light.":[40],"The":[41],"reactions":[42],"delivered":[43],"desired":[44],"benzobicycloheptanone":[46],"products":[47],"excellent":[49],"regioselectivity":[50],"in":[51],"high":[52],"yields":[53],"(up":[54],"96%).":[56],"This":[57],"process":[58],"is":[59],"superior":[60],"syntheses":[63],"benzobicyclo[3.1.1]heptanones,":[65],"which":[66],"are":[67],"readily":[68],"converted":[69],"B-norbenzomorphan":[71],"analogues":[72],"biological":[74],"significance.":[75],"Electrochemical,":[76],"computational,":[77],"and":[78,88],"spectroscopic":[79],"studies":[80],"substantiated":[81],"mechanism":[83],"triplet":[85],"energy":[86],"transfer":[87],"explained":[89],"unusual":[91],"regiocontrol.":[92]},"counts_by_year":[{"year":2026,"cited_by_count":12},{"year":2025,"cited_by_count":12},{"year":2024,"cited_by_count":24},{"year":2023,"cited_by_count":14},{"year":2022,"cited_by_count":19},{"year":2021,"cited_by_count":8},{"year":2020,"cited_by_count":18},{"year":2019,"cited_by_count":17},{"year":2018,"cited_by_count":21},{"year":2017,"cited_by_count":5}],"updated_date":"2026-11-03T10:50:19.383937","created_date":"2017-07-14T00:00:00"}