{"id":"https://openalex.org/W2921770352","doi":"https://doi.org/10.1021/acs.joc.8b03223","title":"Concise Approach to Cyclohexyne and 1,2-Cyclohexadiene Precursors","display_name":"Concise Approach to Cyclohexyne and 1,2-Cyclohexadiene Precursors","publication_year":2019,"publication_date":"2019-03-06","ids":{"openalex":"https://openalex.org/W2921770352","doi":"https://doi.org/10.1021/acs.joc.8b03223","mag":"2921770352","pmid":"https://pubmed.ncbi.nlm.nih.gov/30840455","pmcid":"https://www.ncbi.nlm.nih.gov/pmc/articles/6935045"},"language":"en","primary_location":{"id":"doi:10.1021/acs.joc.8b03223","doi":"https://doi.org/10.1021/acs.joc.8b03223","is_oa":false,"landing_page_url":"https://doi.org/10.1021/acs.joc.8b03223","pdf_url":null,"source":{"id":"https://openalex.org/S205050996","display_name":"The Journal of Organic Chemistry","issn_l":"0022-3263","issn":["0022-3263","1520-6904"],"is_oa":false,"is_in_doaj":false,"is_core":true,"listed_in":["cwts-core","dongbi-a","jufo-2","ki-jl-2","medline","norway-2","poland-140","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":"The Journal of Organic Chemistry","raw_type":"journal-article"},"volume":null,"type":"article","is_traditional":true,"indexed_in":["crossref","pubmed"],"open_access":{"is_oa":true,"oa_status":"green","oa_url":"https://www.ncbi.nlm.nih.gov/pmc/articles/6935045","any_repository_has_fulltext":true},"authorships":[{"author_position":"first","author":{"id":"https://openalex.org/A5020159711","display_name":"Jason V. Chari","orcid":"https://orcid.org/0000-0001-7729-9619","observed_orcids":["https://orcid.org/0000-0001-7729-9619"]},"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":"Jason V. Chari","raw_affiliation_strings":["Department of Biochemistry and Chemistry, University of California, Los Angeles, California 90095, United States"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Department of Biochemistry and Chemistry, University of California, Los Angeles, California 90095, United States","institution_ids":["https://openalex.org/I161318765"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5031641098","display_name":"Francesca M. Ippoliti","orcid":"https://orcid.org/0000-0003-4655-0545","observed_orcids":["https://orcid.org/0000-0003-4655-0545"]},"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":"Francesca M. Ippoliti","raw_affiliation_strings":["Department of Biochemistry and Chemistry, University of California, Los Angeles, California 90095, United States"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Department of Biochemistry and Chemistry, University of California, Los Angeles, California 90095, United States","institution_ids":["https://openalex.org/I161318765"]}]},{"author_position":"last","author":{"id":"https://openalex.org/A5091765956","display_name":"Neil K. Garg","orcid":"https://orcid.org/0000-0002-7793-2629","observed_orcids":["https://orcid.org/0000-0002-7793-2629"]},"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":"Neil K. Garg","raw_affiliation_strings":["Department of Biochemistry and Chemistry, University of California, Los Angeles, California 90095, United States"],"raw_orcid":"https://orcid.org/0000-0002-7793-2629","affiliations":[{"raw_affiliation_string":"Department of Biochemistry and Chemistry, University of California, Los Angeles, California 90095, United States","institution_ids":["https://openalex.org/I161318765"]}]}],"institutions":[],"countries_distinct_count":1,"institutions_distinct_count":1,"corresponding_author_ids":["https://openalex.org/A5091765956"],"corresponding_institution_ids":["https://openalex.org/I161318765"],"apc_list":{"value":5000,"currency":"USD","value_usd":5000},"apc_paid":null,"fwci":1.1217,"has_fulltext":false,"cited_by_count":20,"citation_normalized_percentile":{"value":0.71085055,"is_in_top_1_percent":false,"is_in_top_10_percent":false},"cited_by_percentile_year":{"min":88,"max":98},"biblio":{"volume":"84","issue":"6","first_page":"3652","last_page":"3655"},"is_retracted":false,"is_paratext":false,"is_xpac":false,"primary_topic":{"id":"https://openalex.org/T13859","display_name":"Organic Chemistry Synthesis Methods","score":0.4487000107765198,"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/T13859","display_name":"Organic Chemistry Synthesis Methods","score":0.4487000107765198,"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":0.3495999872684479,"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/T11441","display_name":"Organoboron and organosilicon chemistry","score":0.0885000005364418,"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/cyclohexyne","display_name":"cyclohexyne","score":0.8930000066757202},{"id":"https://openalex.org/keywords/silyl-triflates","display_name":"silyl triflates","score":0.8989999890327454},{"id":"https://openalex.org/keywords/cyclic-alkynes","display_name":"cyclic alkynes","score":0.765999972820282},{"id":"https://openalex.org/keywords/allenes","display_name":"allenes","score":0.9150000214576721},{"id":"https://openalex.org/keywords/cyclohexanone-derivatives","display_name":"cyclohexanone derivatives","score":0.9100000262260437},{"id":"https://openalex.org/keywords/triflation","display_name":"triflation","score":0.9580000042915344},{"id":"https://openalex.org/keywords/strained-alkynes","display_name":"strained alkynes","score":0.7960000038146973},{"id":"https://openalex.org/keywords/synthetic-building-blocks","display_name":"synthetic building blocks","score":0.6669999957084656}],"concepts":[{"id":"https://openalex.org/C21774173","wikidata":"https://www.wikidata.org/wiki/Q2462024","display_name":"Trifluoromethanesulfonate","level":3,"score":0.9386674165725708},{"id":"https://openalex.org/C185592680","wikidata":"https://www.wikidata.org/wiki/Q2329","display_name":"Chemistry","level":0,"score":0.9078928232192993},{"id":"https://openalex.org/C5304478","wikidata":"https://www.wikidata.org/wiki/Q502457","display_name":"Silylation","level":3,"score":0.8769135475158691},{"id":"https://openalex.org/C2780450521","wikidata":"https://www.wikidata.org/wiki/Q409178","display_name":"Cyclohexanone","level":3,"score":0.8137578964233398},{"id":"https://openalex.org/C21951064","wikidata":"https://www.wikidata.org/wiki/Q899212","display_name":"Combinatorial chemistry","level":1,"score":0.5259773135185242},{"id":"https://openalex.org/C111771559","wikidata":"https://www.wikidata.org/wiki/Q66295","display_name":"Derivative (finance)","level":2,"score":0.5220146775245667},{"id":"https://openalex.org/C48044578","wikidata":"https://www.wikidata.org/wiki/Q727490","display_name":"Scalability","level":2,"score":0.4782494604587555},{"id":"https://openalex.org/C178790620","wikidata":"https://www.wikidata.org/wiki/Q11351","display_name":"Organic chemistry","level":1,"score":0.4130200147628784},{"id":"https://openalex.org/C161790260","wikidata":"https://www.wikidata.org/wiki/Q82264","display_name":"Catalysis","level":2,"score":0.12379646301269531},{"id":"https://openalex.org/C77088390","wikidata":"https://www.wikidata.org/wiki/Q8513","display_name":"Database","level":1,"score":0.07548075914382935},{"id":"https://openalex.org/C41008148","wikidata":"https://www.wikidata.org/wiki/Q21198","display_name":"Computer science","level":0,"score":0.07166942954063416},{"id":"https://openalex.org/C106159729","wikidata":"https://www.wikidata.org/wiki/Q2294553","display_name":"Financial economics","level":1,"score":0.0},{"id":"https://openalex.org/C162324750","wikidata":"https://www.wikidata.org/wiki/Q8134","display_name":"Economics","level":0,"score":0.0}],"mesh":[{"descriptor_ui":"D000480","descriptor_name":"Alkynes","qualifier_ui":"Q000138","qualifier_name":"chemical synthesis","is_major_topic":true},{"descriptor_ui":"D000480","descriptor_name":"Alkynes","qualifier_ui":"Q000737","qualifier_name":"chemistry","is_major_topic":false},{"descriptor_ui":"D015394","descriptor_name":"Molecular Structure","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D017646","descriptor_name":"Organosilicon Compounds","qualifier_ui":"Q000737","qualifier_name":"chemistry","is_major_topic":true},{"descriptor_ui":"D053138","descriptor_name":"Cyclohexenes","qualifier_ui":"Q000138","qualifier_name":"chemical synthesis","is_major_topic":true},{"descriptor_ui":"D053138","descriptor_name":"Cyclohexenes","qualifier_ui":"Q000737","qualifier_name":"chemistry","is_major_topic":false}],"locations_count":4,"locations":[{"id":"doi:10.1021/acs.joc.8b03223","doi":"https://doi.org/10.1021/acs.joc.8b03223","is_oa":false,"landing_page_url":"https://doi.org/10.1021/acs.joc.8b03223","pdf_url":null,"source":{"id":"https://openalex.org/S205050996","display_name":"The Journal of Organic Chemistry","issn_l":"0022-3263","issn":["0022-3263","1520-6904"],"is_oa":false,"is_in_doaj":false,"is_core":true,"listed_in":["cwts-core","dongbi-a","jufo-2","ki-jl-2","medline","norway-2","poland-140","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":"The Journal of Organic Chemistry","raw_type":"journal-article"},{"id":"pmid:30840455","doi":null,"is_oa":false,"landing_page_url":"https://pubmed.ncbi.nlm.nih.gov/30840455","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":"The Journal of organic chemistry","raw_type":"Journal Article"},{"id":"pmh:oai:europepmc.org:6007106","doi":null,"is_oa":true,"landing_page_url":"https://www.ncbi.nlm.nih.gov/pmc/articles/6935045","pdf_url":null,"source":{"id":"https://openalex.org/S4306400806","display_name":"Europe PMC (PubMed Central)","issn_l":null,"issn":null,"is_oa":false,"is_in_doaj":false,"is_core":false,"listed_in":[],"host_organization":"https://openalex.org/I1303153112","host_organization_name":"European Bioinformatics Institute","host_organization_lineage":["https://openalex.org/I1303153112"],"host_organization_lineage_names":[],"type":"repository"},"license":null,"license_id":null,"version":"acceptedVersion","is_accepted":true,"is_published":false,"raw_source_name":null,"raw_type":"Text"},{"id":"pmh:oai:pubmedcentral.nih.gov:6935045","doi":null,"is_oa":true,"landing_page_url":"https://pmc.ncbi.nlm.nih.gov/articles/PMC6935045/","pdf_url":null,"source":{"id":"https://openalex.org/S2764455111","display_name":"PubMed Central","issn_l":null,"issn":null,"is_oa":true,"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":"acceptedVersion","is_accepted":true,"is_published":false,"raw_source_name":"J Org Chem","raw_type":"Text"}],"best_oa_location":{"id":"pmh:oai:europepmc.org:6007106","doi":null,"is_oa":true,"landing_page_url":"https://www.ncbi.nlm.nih.gov/pmc/articles/6935045","pdf_url":null,"source":{"id":"https://openalex.org/S4306400806","display_name":"Europe PMC (PubMed Central)","issn_l":null,"issn":null,"is_oa":false,"is_in_doaj":false,"is_core":false,"listed_in":[],"host_organization":"https://openalex.org/I1303153112","host_organization_name":"European Bioinformatics Institute","host_organization_lineage":["https://openalex.org/I1303153112"],"host_organization_lineage_names":[],"type":"repository"},"license":null,"license_id":null,"version":"acceptedVersion","is_accepted":true,"is_published":false,"raw_source_name":null,"raw_type":"Text"},"sustainable_development_goals":[],"study_designs":[],"awards":[{"id":"https://openalex.org/G5402798198","display_name":"Time-of-Flight Mass Spectrometer for Synthesis Supporting Biomedical Research","funder_award_id":"S10RR025631","funder_id":"https://openalex.org/F4320337375","funder_display_name":"National Center for Research Resources"},{"id":"https://openalex.org/G6622060749","display_name":"Harnessing Strained Intermediates to Access Complex Molecules","funder_award_id":"R01GM123299","funder_id":"https://openalex.org/F4320337354","funder_display_name":"National Institute of General Medical Sciences"}],"funders":[{"id":"https://openalex.org/F4320332502","display_name":"University of California, Los Angeles","ror":"https://ror.org/046rm7j60"},{"id":"https://openalex.org/F4320337354","display_name":"National Institute of General Medical Sciences","ror":"https://ror.org/04q48ey07"},{"id":"https://openalex.org/F4320337375","display_name":"National Center for Research Resources","ror":"https://ror.org/04pw6fb54"}],"has_content":{"pdf":false,"grobid_xml":false},"content_urls":null,"referenced_works_count":51,"referenced_works":["https://openalex.org/W1765046296","https://openalex.org/W1831187883","https://openalex.org/W1966859369","https://openalex.org/W1969496843","https://openalex.org/W1984243967","https://openalex.org/W1990605211","https://openalex.org/W1992713013","https://openalex.org/W2000036113","https://openalex.org/W2002528196","https://openalex.org/W2011655519","https://openalex.org/W2024447350","https://openalex.org/W2027471673","https://openalex.org/W2028147077","https://openalex.org/W2035430536","https://openalex.org/W2037143889","https://openalex.org/W2041528267","https://openalex.org/W2052944285","https://openalex.org/W2057296841","https://openalex.org/W2059179323","https://openalex.org/W2059370320","https://openalex.org/W2059479118","https://openalex.org/W2060900382","https://openalex.org/W2061728803","https://openalex.org/W2086623065","https://openalex.org/W2088141919","https://openalex.org/W2092527919","https://openalex.org/W2104662659","https://openalex.org/W2114297300","https://openalex.org/W2131143461","https://openalex.org/W2150099740","https://openalex.org/W2165280480","https://openalex.org/W2165352032","https://openalex.org/W2254773827","https://openalex.org/W2308028296","https://openalex.org/W2318308937","https://openalex.org/W2322862376","https://openalex.org/W2323179079","https://openalex.org/W2324113754","https://openalex.org/W2395329757","https://openalex.org/W2479229781","https://openalex.org/W2552179254","https://openalex.org/W2593653013","https://openalex.org/W2643165901","https://openalex.org/W2732097727","https://openalex.org/W2769992878","https://openalex.org/W2798137214","https://openalex.org/W2808579343","https://openalex.org/W2884399757","https://openalex.org/W2898468335","https://openalex.org/W2917146951","https://openalex.org/W2949693996"],"related_works":["https://openalex.org/W2909746357","https://openalex.org/W2798137214","https://openalex.org/W3026817014","https://openalex.org/W4206153741","https://openalex.org/W2160419549","https://openalex.org/W2951502405","https://openalex.org/W2582408384","https://openalex.org/W2887451975","https://openalex.org/W7130317957","https://openalex.org/W2131143461"],"abstract_inverted_index":{"Silyl":[0],"triflate":[1,26],"precursors":[2,27],"to":[3,22,28],"cyclic":[4],"alkynes":[5,60],"and":[6,18,30,61],"allenes":[7,62],"serve":[8],"as":[9],"valuable":[10],"synthetic":[11,20],"building":[12],"blocks.":[13],"We":[14],"report":[15],"a":[16,35],"concise":[17],"scalable":[19],"approach":[21],"prepare":[23],"the":[24,55],"silyl":[25],"cyclohexyne":[29],"1,2-cyclohexadiene.":[31],"The":[32],"strategy":[33],"involves":[34],"retro-Brook":[36],"rearrangement":[37],"of":[38,58],"an":[39],"easily":[40],"accessible":[41],"cyclohexanone":[42],"derivative,":[43],"followed":[44],"by":[45],"triflation":[46],"protocols.":[47],"This":[48],"simple,":[49],"yet":[50],"controlled,":[51],"method":[52],"should":[53],"enable":[54],"further":[56],"study":[57],"strained":[59],"in":[63],"chemical":[64],"synthesis.":[65]},"counts_by_year":[{"year":2026,"cited_by_count":2},{"year":2025,"cited_by_count":2},{"year":2024,"cited_by_count":3},{"year":2023,"cited_by_count":1},{"year":2022,"cited_by_count":2},{"year":2021,"cited_by_count":6},{"year":2020,"cited_by_count":3},{"year":2019,"cited_by_count":1}],"updated_date":"2026-11-10T11:39:43.021295","created_date":"2019-03-22T00:00:00"}