{"id":"https://openalex.org/W2020703322","doi":"https://doi.org/10.1021/ja045694g","title":"Cp*RuCl-Catalyzed [2 + 2 + 2] Cycloadditions of \u03b1,\u03c9-Diynes with Electron-Deficient Carbon\u2212Heteroatom Multiple Bonds Leading to Heterocycles","display_name":"Cp*RuCl-Catalyzed [2 + 2 + 2] Cycloadditions of \u03b1,\u03c9-Diynes with Electron-Deficient Carbon\u2212Heteroatom Multiple Bonds Leading to Heterocycles","publication_year":2004,"publication_date":"2004-12-14","ids":{"openalex":"https://openalex.org/W2020703322","doi":"https://doi.org/10.1021/ja045694g","mag":"2020703322","pmid":"https://pubmed.ncbi.nlm.nih.gov/15643884"},"language":"en","primary_location":{"id":"doi:10.1021/ja045694g","doi":"https://doi.org/10.1021/ja045694g","is_oa":false,"landing_page_url":"https://doi.org/10.1021/ja045694g","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","is_traditional":true,"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/A5067407925","display_name":"Yoshihiko Yamamoto","orcid":"https://orcid.org/0000-0001-8544-6324","observed_orcids":["https://orcid.org/0000-0001-8544-6324"]},"institutions":[{"id":"https://openalex.org/I60134161","display_name":"Nagoya University","ror":"https://ror.org/04chrp450","country_code":"JP","type":"education","lineage":["https://openalex.org/I60134161"]}],"countries":["JP"],"is_corresponding":false,"raw_author_name":"Yoshihiko Yamamoto","raw_affiliation_strings":["Contribution from the Department of Applied Chemistry and Department of Molecular Design and Engineering, Graduate School of Engineering, Nagoya University, Chikusa, Nagoya 464-8603, Japan"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Contribution from the Department of Applied Chemistry and Department of Molecular Design and Engineering, Graduate School of Engineering, Nagoya University, Chikusa, Nagoya 464-8603, Japan","institution_ids":["https://openalex.org/I60134161"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5023231109","display_name":"Keisuke Kinpara","orcid":null,"observed_orcids":[]},"institutions":[{"id":"https://openalex.org/I60134161","display_name":"Nagoya University","ror":"https://ror.org/04chrp450","country_code":"JP","type":"education","lineage":["https://openalex.org/I60134161"]}],"countries":["JP"],"is_corresponding":false,"raw_author_name":"Keisuke Kinpara","raw_affiliation_strings":["Contribution from the Department of Applied Chemistry and Department of Molecular Design and Engineering, Graduate School of Engineering, Nagoya University, Chikusa, Nagoya 464-8603, Japan"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Contribution from the Department of Applied Chemistry and Department of Molecular Design and Engineering, Graduate School of Engineering, Nagoya University, Chikusa, Nagoya 464-8603, Japan","institution_ids":["https://openalex.org/I60134161"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5056117815","display_name":"Tomoaki Saigoku","orcid":null,"observed_orcids":[]},"institutions":[{"id":"https://openalex.org/I60134161","display_name":"Nagoya University","ror":"https://ror.org/04chrp450","country_code":"JP","type":"education","lineage":["https://openalex.org/I60134161"]}],"countries":["JP"],"is_corresponding":false,"raw_author_name":"Tomoaki Saigoku","raw_affiliation_strings":["Contribution from the Department of Applied Chemistry and Department of Molecular Design and Engineering, Graduate School of Engineering, Nagoya University, Chikusa, Nagoya 464-8603, Japan"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Contribution from the Department of Applied Chemistry and Department of Molecular Design and Engineering, Graduate School of Engineering, Nagoya University, Chikusa, Nagoya 464-8603, Japan","institution_ids":["https://openalex.org/I60134161"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5084680347","display_name":"Hideyuki Takagishi","orcid":"https://orcid.org/0000-0003-2609-5549","observed_orcids":["https://orcid.org/0000-0003-2609-5549"]},"institutions":[{"id":"https://openalex.org/I60134161","display_name":"Nagoya University","ror":"https://ror.org/04chrp450","country_code":"JP","type":"education","lineage":["https://openalex.org/I60134161"]}],"countries":["JP"],"is_corresponding":false,"raw_author_name":"Hideyuki Takagishi","raw_affiliation_strings":["Contribution from the Department of Applied Chemistry and Department of Molecular Design and Engineering, Graduate School of Engineering, Nagoya University, Chikusa, Nagoya 464-8603, Japan"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Contribution from the Department of Applied Chemistry and Department of Molecular Design and Engineering, Graduate School of Engineering, Nagoya University, Chikusa, Nagoya 464-8603, Japan","institution_ids":["https://openalex.org/I60134161"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5102795269","display_name":"Satoshi Okuda","orcid":"https://orcid.org/0000-0002-3774-0294","observed_orcids":["https://orcid.org/0000-0002-3774-0294"]},"institutions":[{"id":"https://openalex.org/I60134161","display_name":"Nagoya University","ror":"https://ror.org/04chrp450","country_code":"JP","type":"education","lineage":["https://openalex.org/I60134161"]}],"countries":["JP"],"is_corresponding":false,"raw_author_name":"Satoshi Okuda","raw_affiliation_strings":["Contribution from the Department of Applied Chemistry and Department of Molecular Design and Engineering, Graduate School of Engineering, Nagoya University, Chikusa, Nagoya 464-8603, Japan"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Contribution from the Department of Applied Chemistry and Department of Molecular Design and Engineering, Graduate School of Engineering, Nagoya University, Chikusa, Nagoya 464-8603, Japan","institution_ids":["https://openalex.org/I60134161"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5110765971","display_name":"Hisao Nishiyama","orcid":null,"observed_orcids":[]},"institutions":[{"id":"https://openalex.org/I60134161","display_name":"Nagoya University","ror":"https://ror.org/04chrp450","country_code":"JP","type":"education","lineage":["https://openalex.org/I60134161"]}],"countries":["JP"],"is_corresponding":false,"raw_author_name":"Hisao Nishiyama","raw_affiliation_strings":["Contribution from the Department of Applied Chemistry and Department of Molecular Design and Engineering, Graduate School of Engineering, Nagoya University, Chikusa, Nagoya 464-8603, Japan"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Contribution from the Department of Applied Chemistry and Department of Molecular Design and Engineering, Graduate School of Engineering, Nagoya University, Chikusa, Nagoya 464-8603, Japan","institution_ids":["https://openalex.org/I60134161"]}]},{"author_position":"last","author":{"id":"https://openalex.org/A5103529960","display_name":"Kenji Itoh","orcid":null,"observed_orcids":[]},"institutions":[{"id":"https://openalex.org/I60134161","display_name":"Nagoya University","ror":"https://ror.org/04chrp450","country_code":"JP","type":"education","lineage":["https://openalex.org/I60134161"]}],"countries":["JP"],"is_corresponding":false,"raw_author_name":"Kenji Itoh","raw_affiliation_strings":["Contribution from the Department of Applied Chemistry and Department of Molecular Design and Engineering, Graduate School of Engineering, Nagoya University, Chikusa, Nagoya 464-8603, Japan"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Contribution from the Department of Applied Chemistry and Department of Molecular Design and Engineering, Graduate School of Engineering, Nagoya University, Chikusa, Nagoya 464-8603, Japan","institution_ids":["https://openalex.org/I60134161"]}]}],"institutions":[],"countries_distinct_count":1,"institutions_distinct_count":1,"corresponding_author_ids":[],"corresponding_institution_ids":["https://openalex.org/I60134161"],"apc_list":{"value":4500,"currency":"USD","value_usd":4500},"apc_paid":null,"fwci":6.6818,"has_fulltext":false,"cited_by_count":262,"citation_normalized_percentile":{"value":0.98009421,"is_in_top_1_percent":false,"is_in_top_10_percent":true},"cited_by_percentile_year":{"min":96,"max":100},"biblio":{"volume":"127","issue":"2","first_page":"605","last_page":"613"},"is_retracted":false,"is_paratext":false,"is_xpac":false,"primary_topic":{"id":"https://openalex.org/T10871","display_name":"Catalytic Alkyne Reactions","score":0.9589999914169312,"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/T10871","display_name":"Catalytic Alkyne Reactions","score":0.9589999914169312,"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/T10354","display_name":"Catalytic C\u2013H Functionalization Methods","score":0.02160000056028366,"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/T10092","display_name":"Organometallic Complex Synthesis and Catalysis","score":0.005799999926239252,"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/ruthenium-catalysis","display_name":"ruthenium catalysis","score":0.9390000104904175},{"id":"https://openalex.org/keywords/2-2-2-cycloaddition","display_name":"[2+2+2] cycloaddition","score":0.9010000228881836},{"id":"https://openalex.org/keywords/1-6-diynes","display_name":"1,6-diynes","score":0.8309999704360962},{"id":"https://openalex.org/keywords/heterocumulenes","display_name":"heterocumulenes","score":0.9819999933242798},{"id":"https://openalex.org/keywords/heterocycle-synthesis","display_name":"heterocyclic synthesis","score":0.8040000200271606},{"id":"https://openalex.org/keywords/pyridones","display_name":"pyridones","score":0.9520000219345093},{"id":"https://openalex.org/keywords/regioselectivity","display_name":"regioselectivity","score":0.9769999980926514},{"id":"https://openalex.org/keywords/chemoselectivity","display_name":"chemoselectivity","score":0.6830000281333923},{"id":"https://openalex.org/keywords/ethyl-propiolate","display_name":"ethyl propiolate","score":0.8539999723434448},{"id":"https://openalex.org/keywords/ethyl-cyanoformate","display_name":"ethyl cyanoformate","score":0.9760000109672546},{"id":"https://openalex.org/keywords/reaction-mechanism","display_name":"reaction mechanism","score":0.7269999980926514}],"concepts":[{"id":"https://openalex.org/C185592680","wikidata":"https://www.wikidata.org/wiki/Q2329","display_name":"Chemistry","level":0,"score":0.9799129366874695},{"id":"https://openalex.org/C59759590","wikidata":"https://www.wikidata.org/wiki/Q2275927","display_name":"Regioselectivity","level":3,"score":0.8679409027099609},{"id":"https://openalex.org/C20950531","wikidata":"https://www.wikidata.org/wiki/Q161940","display_name":"Heteroatom","level":3,"score":0.7431983947753906},{"id":"https://openalex.org/C161790260","wikidata":"https://www.wikidata.org/wiki/Q82264","display_name":"Catalysis","level":2,"score":0.6486300230026245},{"id":"https://openalex.org/C2779485729","wikidata":"https://www.wikidata.org/wiki/Q210385","display_name":"Pyridine","level":2,"score":0.644461989402771},{"id":"https://openalex.org/C155647269","wikidata":"https://www.wikidata.org/wiki/Q243455","display_name":"Medicinal chemistry","level":1,"score":0.597101628780365},{"id":"https://openalex.org/C555196967","wikidata":"https://www.wikidata.org/wiki/Q1086","display_name":"Ruthenium","level":3,"score":0.559583842754364},{"id":"https://openalex.org/C12556323","wikidata":"https://www.wikidata.org/wiki/Q903233","display_name":"Electron deficiency","level":2,"score":0.5073243975639343},{"id":"https://openalex.org/C2780534471","wikidata":"https://www.wikidata.org/wiki/Q408365","display_name":"Isocyanate","level":3,"score":0.4559382498264313},{"id":"https://openalex.org/C24961977","wikidata":"https://www.wikidata.org/wiki/Q225972","display_name":"Bicyclic molecule","level":2,"score":0.4161384403705597},{"id":"https://openalex.org/C71240020","wikidata":"https://www.wikidata.org/wiki/Q186011","display_name":"Stereochemistry","level":1,"score":0.34967413544654846},{"id":"https://openalex.org/C178790620","wikidata":"https://www.wikidata.org/wiki/Q11351","display_name":"Organic chemistry","level":1,"score":0.3230772018432617},{"id":"https://openalex.org/C2780378348","wikidata":"https://www.wikidata.org/wiki/Q25351438","display_name":"Ring (chemistry)","level":2,"score":0.22034507989883423},{"id":"https://openalex.org/C2779578285","wikidata":"https://www.wikidata.org/wiki/Q146322","display_name":"Polyurethane","level":2,"score":0.0}],"mesh":[],"locations_count":4,"locations":[{"id":"doi:10.1021/ja045694g","doi":"https://doi.org/10.1021/ja045694g","is_oa":false,"landing_page_url":"https://doi.org/10.1021/ja045694g","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:15643884","doi":null,"is_oa":false,"landing_page_url":"https://pubmed.ncbi.nlm.nih.gov/15643884","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"},{"id":"pmh:oai:irdb.nii.ac.jp:00897:0003989069","doi":null,"is_oa":false,"landing_page_url":"http://t2r2.star.titech.ac.jp/cgi-bin/publicationinfo.cgi?q_publication_content_number=CTT100521210","pdf_url":null,"source":{"id":"https://openalex.org/S7407056385","display_name":"Institutional Repositories DataBase (IRDB)","issn_l":null,"issn":null,"is_oa":false,"is_in_doaj":false,"is_core":false,"listed_in":[],"host_organization":"https://openalex.org/I184597095","host_organization_name":"National Institute of Informatics","host_organization_lineage":["https://openalex.org/I184597095"],"host_organization_lineage_names":[],"type":"repository"},"license":null,"license_id":null,"version":"submittedVersion","is_accepted":false,"is_published":false,"raw_source_name":"Journal of the American Chemical Society","raw_type":"journal article"},{"id":"pmh:oai:t2r2.star.titech.ac.jp:00225115","doi":null,"is_oa":false,"landing_page_url":"http://t2r2.star.titech.ac.jp/cgi-bin/publicationinfo.cgi?q_publication_content_number=CTT100521210","pdf_url":null,"source":{"id":"https://openalex.org/S4377196385","display_name":"Tokyo Tech Research Repository (Tokyo Institute of Technology)","issn_l":null,"issn":null,"is_oa":false,"is_in_doaj":false,"is_core":false,"listed_in":[],"host_organization":"https://openalex.org/I114531698","host_organization_name":"Tokyo Institute of Technology","host_organization_lineage":["https://openalex.org/I114531698"],"host_organization_lineage_names":[],"type":"repository"},"license":null,"license_id":null,"version":"submittedVersion","is_accepted":false,"is_published":false,"raw_source_name":"","raw_type":"Journal Article"}],"best_oa_location":null,"sustainable_development_goals":[],"study_designs":[],"awards":[],"funders":[],"has_content":{"grobid_xml":false,"pdf":false},"content_urls":null,"referenced_works_count":45,"referenced_works":["https://openalex.org/W192525312","https://openalex.org/W245126800","https://openalex.org/W1967430682","https://openalex.org/W1968012345","https://openalex.org/W1968795072","https://openalex.org/W1972775599","https://openalex.org/W1980094516","https://openalex.org/W1982182382","https://openalex.org/W1987969500","https://openalex.org/W1989539078","https://openalex.org/W1993091495","https://openalex.org/W1994596533","https://openalex.org/W1997016695","https://openalex.org/W1998912997","https://openalex.org/W2003192950","https://openalex.org/W2008041424","https://openalex.org/W2010640773","https://openalex.org/W2017758076","https://openalex.org/W2023191686","https://openalex.org/W2037455810","https://openalex.org/W2042814116","https://openalex.org/W2046997193","https://openalex.org/W2047494966","https://openalex.org/W2049446153","https://openalex.org/W2054246966","https://openalex.org/W2054448566","https://openalex.org/W2057369785","https://openalex.org/W2064629917","https://openalex.org/W2073529495","https://openalex.org/W2073789620","https://openalex.org/W2086957099","https://openalex.org/W2093721184","https://openalex.org/W2096225311","https://openalex.org/W2133994501","https://openalex.org/W2155413913","https://openalex.org/W2159489425","https://openalex.org/W2168938609","https://openalex.org/W2334194629","https://openalex.org/W2938458199","https://openalex.org/W2951160315","https://openalex.org/W3005026542","https://openalex.org/W3024085118","https://openalex.org/W4233638542","https://openalex.org/W4249545014","https://openalex.org/W4388253205"],"related_works":["https://openalex.org/W2020037864","https://openalex.org/W2063380868","https://openalex.org/W1996372003","https://openalex.org/W1984666297","https://openalex.org/W1970591487","https://openalex.org/W2130260514","https://openalex.org/W2052237598","https://openalex.org/W1989766132","https://openalex.org/W1991915291","https://openalex.org/W2949580526"],"abstract_inverted_index":{"In":[0],"the":[1,33,45,66],"presence":[2],"of":[3,7,32,37,47,52,65],"a":[4],"catalytic":[5],"amount":[6],"Cp*RuCl(cod),":[8],"1,6-diynes":[9],"were":[10,42],"allowed":[11],"to":[12,26,63],"react":[13],"chemo-":[14],"and":[15,20,40],"regioselectively":[16],"with":[17,55],"electron-deficient":[18],"nitriles":[19],"heterocumulenes":[21],"at":[22],"60-90":[23],"degrees":[24],"C":[25],"afford":[27],"heterocyclic":[28],"compounds.":[29],"The":[30],"mechanism":[31],"ruthenium-catalyzed":[34],"regioselective":[35],"formations":[36],"bicyclic":[38],"pyridines":[39],"pyridones":[41],"analyzed":[43],"on":[44],"basis":[46],"density":[48],"functional":[49],"calculations.":[50],"Cyclocotrimerizations":[51],"ethyl":[53,56],"propiolate":[54],"cyanoformate":[57],"or":[58,70],"propyl":[59],"isocyanate":[60],"gave":[61],"rise":[62],"two":[64],"four":[67],"possible":[68],"pyridine":[69],"pyridone":[71],"regioisomers.":[72]},"counts_by_year":[{"year":2026,"cited_by_count":3},{"year":2025,"cited_by_count":7},{"year":2024,"cited_by_count":5},{"year":2023,"cited_by_count":6},{"year":2022,"cited_by_count":9},{"year":2021,"cited_by_count":12},{"year":2020,"cited_by_count":6},{"year":2019,"cited_by_count":13},{"year":2018,"cited_by_count":17},{"year":2017,"cited_by_count":17},{"year":2016,"cited_by_count":13},{"year":2015,"cited_by_count":10},{"year":2014,"cited_by_count":13},{"year":2013,"cited_by_count":18},{"year":2012,"cited_by_count":10}],"updated_date":"2026-11-12T12:28:57.059296","created_date":"2016-06-24T00:00:00"}