{"id":"https://openalex.org/W2952028639","doi":"https://doi.org/10.1021/ol203392r","title":"Synthesis of N-Azolylindoles by Copper-Catalyzed C\u2013H/N\u2013H Coupling\u2013Annulation Sequence of o-Alkynylanilines","display_name":"Synthesis of N-Azolylindoles by Copper-Catalyzed C\u2013H/N\u2013H Coupling\u2013Annulation Sequence of o-Alkynylanilines","publication_year":2012,"publication_date":"2012-01-11","ids":{"openalex":"https://openalex.org/W2952028639","doi":"https://doi.org/10.1021/ol203392r","mag":"2952028639","pmid":"https://pubmed.ncbi.nlm.nih.gov/22236326"},"language":"en","primary_location":{"id":"doi:10.1021/ol203392r","doi":"https://doi.org/10.1021/ol203392r","is_oa":false,"landing_page_url":"https://doi.org/10.1021/ol203392r","pdf_url":null,"source":{"id":"https://openalex.org/S201989124","display_name":"Organic Letters","issn_l":"1523-7052","issn":["1523-7052","1523-7060"],"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":"Organic Letters","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/A5032565002","display_name":"Yoshiro Oda","orcid":null,"observed_orcids":[]},"institutions":[{"id":"https://openalex.org/I98285908","display_name":"The University of Osaka","ror":"https://ror.org/035t8zc32","country_code":"JP","type":"education","lineage":["https://openalex.org/I98285908"]}],"countries":["JP"],"is_corresponding":false,"raw_author_name":"Yoshiro Oda","raw_affiliation_strings":["Department of Applied Chemistry, Faculty of Engineering, Osaka University, Suita, Osaka 565-0871, Japan"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Department of Applied Chemistry, Faculty of Engineering, Osaka University, Suita, Osaka 565-0871, Japan","institution_ids":["https://openalex.org/I98285908"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5023893245","display_name":"Koji Hirano","orcid":"https://orcid.org/0000-0001-9752-1985","observed_orcids":["https://orcid.org/0000-0001-9752-1985"]},"institutions":[{"id":"https://openalex.org/I98285908","display_name":"The University of Osaka","ror":"https://ror.org/035t8zc32","country_code":"JP","type":"education","lineage":["https://openalex.org/I98285908"]}],"countries":["JP"],"is_corresponding":true,"raw_author_name":"Koji Hirano","raw_affiliation_strings":["Department of Applied Chemistry, Faculty of Engineering, Osaka University, Suita, Osaka 565-0871, Japan"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Department of Applied Chemistry, Faculty of Engineering, Osaka University, Suita, Osaka 565-0871, Japan","institution_ids":["https://openalex.org/I98285908"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5083056412","display_name":"Tetsuya Satoh","orcid":"https://orcid.org/0000-0002-1792-140X","observed_orcids":["https://orcid.org/0000-0002-1792-140X"]},"institutions":[{"id":"https://openalex.org/I98285908","display_name":"The University of Osaka","ror":"https://ror.org/035t8zc32","country_code":"JP","type":"education","lineage":["https://openalex.org/I98285908"]}],"countries":["JP"],"is_corresponding":false,"raw_author_name":"Tetsuya Satoh","raw_affiliation_strings":["Department of Applied Chemistry, Faculty of Engineering, Osaka University, Suita, Osaka 565-0871, Japan"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Department of Applied Chemistry, Faculty of Engineering, Osaka University, Suita, Osaka 565-0871, Japan","institution_ids":["https://openalex.org/I98285908"]}]},{"author_position":"last","author":{"id":"https://openalex.org/A5028632795","display_name":"Masahiro Miura","orcid":"https://orcid.org/0000-0001-8288-6439","observed_orcids":["https://orcid.org/0000-0001-8288-6439"]},"institutions":[{"id":"https://openalex.org/I98285908","display_name":"The University of Osaka","ror":"https://ror.org/035t8zc32","country_code":"JP","type":"education","lineage":["https://openalex.org/I98285908"]}],"countries":["JP"],"is_corresponding":true,"raw_author_name":"Masahiro Miura","raw_affiliation_strings":["Department of Applied Chemistry, Faculty of Engineering, Osaka University, Suita, Osaka 565-0871, Japan"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Department of Applied Chemistry, Faculty of Engineering, Osaka University, Suita, Osaka 565-0871, Japan","institution_ids":["https://openalex.org/I98285908"]}]}],"institutions":[],"countries_distinct_count":1,"institutions_distinct_count":1,"corresponding_author_ids":["https://openalex.org/A5023893245","https://openalex.org/A5028632795"],"corresponding_institution_ids":["https://openalex.org/I98285908"],"apc_list":{"value":4500,"currency":"USD","value_usd":4500},"apc_paid":null,"fwci":4.5622,"has_fulltext":false,"cited_by_count":62,"citation_normalized_percentile":{"value":0.95582336,"is_in_top_1_percent":false,"is_in_top_10_percent":true},"cited_by_percentile_year":{"min":89,"max":99},"biblio":{"volume":"14","issue":"2","first_page":"664","last_page":"667"},"is_retracted":false,"is_paratext":false,"is_xpac":false,"primary_topic":{"id":"https://openalex.org/T10354","display_name":"Catalytic C\u2013H Functionalization Methods","score":0.9951000213623047,"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/T10354","display_name":"Catalytic C\u2013H Functionalization Methods","score":0.9951000213623047,"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":0.00139999995008111,"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/T12189","display_name":"Sulfur-Based Synthesis Techniques","score":0.0010000000474974513,"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/copper-catalysis","display_name":"copper catalysis","score":0.8130000233650208},{"id":"https://openalex.org/keywords/benzannulation","display_name":"benzannulation","score":0.8009999990463257},{"id":"https://openalex.org/keywords/o-alkynylanilines","display_name":"o-alkynylanilines","score":0.9589999914169312},{"id":"https://openalex.org/keywords/cascade-reactions","display_name":"cascade reactions","score":0.8220000267028809},{"id":"https://openalex.org/keywords/molecular-oxygen-oxidant","display_name":"molecular oxygen oxidant","score":0.765999972820282},{"id":"https://openalex.org/keywords/azoles","display_name":"azoles","score":0.6299999952316284}],"concepts":[{"id":"https://openalex.org/C2776416436","wikidata":"https://www.wikidata.org/wiki/Q3751781","display_name":"Domino","level":3,"score":0.7988226413726807},{"id":"https://openalex.org/C185592680","wikidata":"https://www.wikidata.org/wiki/Q2329","display_name":"Chemistry","level":0,"score":0.7870497703552246},{"id":"https://openalex.org/C7512685","wikidata":"https://www.wikidata.org/wiki/Q529093","display_name":"Annulation","level":3,"score":0.6645817756652832},{"id":"https://openalex.org/C2778112365","wikidata":"https://www.wikidata.org/wiki/Q3511065","display_name":"Sequence (biology)","level":2,"score":0.6236602663993835},{"id":"https://openalex.org/C161790260","wikidata":"https://www.wikidata.org/wiki/Q82264","display_name":"Catalysis","level":2,"score":0.6007470488548279},{"id":"https://openalex.org/C131584629","wikidata":"https://www.wikidata.org/wiki/Q4308705","display_name":"Coupling (piping)","level":2,"score":0.5802793502807617},{"id":"https://openalex.org/C544778455","wikidata":"https://www.wikidata.org/wiki/Q753","display_name":"Copper","level":2,"score":0.5623945593833923},{"id":"https://openalex.org/C21951064","wikidata":"https://www.wikidata.org/wiki/Q899212","display_name":"Combinatorial chemistry","level":1,"score":0.5548037886619568},{"id":"https://openalex.org/C2992086430","wikidata":"https://www.wikidata.org/wiki/Q428653","display_name":"Molecular oxygen","level":3,"score":0.4196256697177887},{"id":"https://openalex.org/C71240020","wikidata":"https://www.wikidata.org/wiki/Q186011","display_name":"Stereochemistry","level":1,"score":0.36911696195602417},{"id":"https://openalex.org/C155647269","wikidata":"https://www.wikidata.org/wiki/Q243455","display_name":"Medicinal chemistry","level":1,"score":0.3373448848724365},{"id":"https://openalex.org/C178790620","wikidata":"https://www.wikidata.org/wiki/Q11351","display_name":"Organic chemistry","level":1,"score":0.20763379335403442},{"id":"https://openalex.org/C192562407","wikidata":"https://www.wikidata.org/wiki/Q228736","display_name":"Materials science","level":0,"score":0.050078630447387695},{"id":"https://openalex.org/C191897082","wikidata":"https://www.wikidata.org/wiki/Q11467","display_name":"Metallurgy","level":1,"score":0.0},{"id":"https://openalex.org/C55493867","wikidata":"https://www.wikidata.org/wiki/Q7094","display_name":"Biochemistry","level":1,"score":0.0}],"mesh":[],"locations_count":2,"locations":[{"id":"doi:10.1021/ol203392r","doi":"https://doi.org/10.1021/ol203392r","is_oa":false,"landing_page_url":"https://doi.org/10.1021/ol203392r","pdf_url":null,"source":{"id":"https://openalex.org/S201989124","display_name":"Organic Letters","issn_l":"1523-7052","issn":["1523-7052","1523-7060"],"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":"Organic Letters","raw_type":"journal-article"},{"id":"pmid:22236326","doi":null,"is_oa":false,"landing_page_url":"https://pubmed.ncbi.nlm.nih.gov/22236326","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":"Organic letters","raw_type":"Journal Article"}],"best_oa_location":null,"sustainable_development_goals":[],"study_designs":[],"awards":[{"id":"https://openalex.org/G987262815","display_name":"Development of Environmentally Benign Biaryl Couplings Based on Nickel Catalysts","funder_award_id":"22750040","funder_id":"https://openalex.org/F4320334764","funder_display_name":"Japan Society for the Promotion of Science"}],"funders":[{"id":"https://openalex.org/F4320334764","display_name":"Japan Society for the Promotion of Science","ror":"https://ror.org/00hhkn466"}],"has_content":{"grobid_xml":false,"pdf":false},"content_urls":null,"referenced_works_count":58,"referenced_works":["https://openalex.org/W1977988158","https://openalex.org/W1981288459","https://openalex.org/W1989631271","https://openalex.org/W1989852382","https://openalex.org/W1991184360","https://openalex.org/W1997770703","https://openalex.org/W2000951812","https://openalex.org/W2005092589","https://openalex.org/W2006129655","https://openalex.org/W2007594170","https://openalex.org/W2010101793","https://openalex.org/W2012867612","https://openalex.org/W2013478843","https://openalex.org/W2013980945","https://openalex.org/W2019568660","https://openalex.org/W2020086870","https://openalex.org/W2020419388","https://openalex.org/W2028695331","https://openalex.org/W2031644569","https://openalex.org/W2033898754","https://openalex.org/W2035607313","https://openalex.org/W2038452922","https://openalex.org/W2040309264","https://openalex.org/W2047648221","https://openalex.org/W2061012320","https://openalex.org/W2061846059","https://openalex.org/W2063559756","https://openalex.org/W2065382371","https://openalex.org/W2071936450","https://openalex.org/W2075073048","https://openalex.org/W2083990575","https://openalex.org/W2088948925","https://openalex.org/W2089632015","https://openalex.org/W2101373633","https://openalex.org/W2114029367","https://openalex.org/W2114118231","https://openalex.org/W2126109732","https://openalex.org/W2128969383","https://openalex.org/W2129966569","https://openalex.org/W2143014353","https://openalex.org/W2155390912","https://openalex.org/W2163549702","https://openalex.org/W2164425336","https://openalex.org/W2167125671","https://openalex.org/W2179162529","https://openalex.org/W2318403847","https://openalex.org/W2321508571","https://openalex.org/W2324235004","https://openalex.org/W2325072690","https://openalex.org/W2326535103","https://openalex.org/W2326587253","https://openalex.org/W2327405877","https://openalex.org/W2328176497","https://openalex.org/W2331229388","https://openalex.org/W2949407522","https://openalex.org/W2950041319","https://openalex.org/W2950618072","https://openalex.org/W2952737027"],"related_works":["https://openalex.org/W1984698372","https://openalex.org/W2060086389","https://openalex.org/W2951908269","https://openalex.org/W2750660792","https://openalex.org/W2977057258","https://openalex.org/W2002912822","https://openalex.org/W2065382371","https://openalex.org/W1999018046","https://openalex.org/W2989328842","https://openalex.org/W3014276757"],"abstract_inverted_index":{"A":[0],"wide":[1],"range":[2],"of":[3,46],"o-alkynylanilines":[4],"undergo":[5],"a":[6,38],"copper-catalyzed":[7],"direct":[8],"C-H/N-H":[9],"coupling":[10],"with":[11,29],"azoles":[12],"followed":[13],"by":[14],"benzannulation":[15],"to":[16,42],"form":[17],"the":[18,33,43],"corresponding":[19],"N-azolylindoles":[20],"in":[21,48],"good":[22],"yields.":[23],"The":[24],"domino":[25],"reaction":[26],"proceeds":[27],"effectively":[28],"molecular":[30],"oxygen":[31],"as":[32],"sole":[34],"oxidant":[35],"and":[36,50],"provides":[37],"new":[39],"dehydrogenative":[40],"access":[41],"titled":[44],"compounds":[45],"interest":[47],"pharmaceutical":[49],"material":[51],"sciences.":[52]},"counts_by_year":[{"year":2025,"cited_by_count":1},{"year":2024,"cited_by_count":2},{"year":2023,"cited_by_count":3},{"year":2022,"cited_by_count":6},{"year":2021,"cited_by_count":3},{"year":2020,"cited_by_count":3},{"year":2019,"cited_by_count":1},{"year":2018,"cited_by_count":2},{"year":2017,"cited_by_count":4},{"year":2016,"cited_by_count":6},{"year":2015,"cited_by_count":3},{"year":2014,"cited_by_count":11},{"year":2013,"cited_by_count":8},{"year":2012,"cited_by_count":9}],"updated_date":"2026-08-21T09:56:20.448147","created_date":"2019-06-27T00:00:00"}
