{"id":"https://openalex.org/W2018823964","doi":"https://doi.org/10.1021/ja0173019","title":"Mild Iridium-Catalyzed Borylation of Arenes. High Turnover Numbers, Room Temperature Reactions, and Isolation of a Potential Intermediate","display_name":"Mild Iridium-Catalyzed Borylation of Arenes. High Turnover Numbers, Room Temperature Reactions, and Isolation of a Potential Intermediate","publication_year":2001,"publication_date":"2001-12-28","ids":{"openalex":"https://openalex.org/W2018823964","doi":"https://doi.org/10.1021/ja0173019","mag":"2018823964","pmid":"https://pubmed.ncbi.nlm.nih.gov/11792205"},"language":"en","primary_location":{"id":"doi:10.1021/ja0173019","doi":"https://doi.org/10.1021/ja0173019","is_oa":false,"landing_page_url":"https://doi.org/10.1021/ja0173019","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"},"parent_works":[],"lineage":["https://openalex.org/W2018823964"],"child_works_count":0,"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/A5089875782","display_name":"Tatsuo Ishiyama","orcid":null,"observed_orcids":[]},"institutions":[{"id":"https://openalex.org/I32971472","display_name":"Yale University","ror":"https://ror.org/03v76x132","country_code":"US","type":"education","lineage":["https://openalex.org/I32971472"]}],"countries":["US"],"is_corresponding":false,"raw_author_name":"Tatsuo Ishiyama","raw_affiliation_strings":["Department of Chemistry, Yale University, P.O. Box 208107, New Haven, Connecticut 06520-8107, USA"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Department of Chemistry, Yale University, P.O. Box 208107, New Haven, Connecticut 06520-8107, USA","institution_ids":["https://openalex.org/I32971472"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5090966671","display_name":"Jun S. Takagi","orcid":"https://orcid.org/0009-0000-1547-6915","observed_orcids":["https://orcid.org/0009-0000-1547-6915","https://orcid.org/0009-0003-2634-9665"]},"institutions":[{"id":"https://openalex.org/I205349734","display_name":"Hokkaido University","ror":"https://ror.org/02e16g702","country_code":"JP","type":"education","lineage":["https://openalex.org/I205349734"]},{"id":"https://openalex.org/I32971472","display_name":"Yale University","ror":"https://ror.org/03v76x132","country_code":"US","type":"education","lineage":["https://openalex.org/I32971472"]}],"countries":["JP","US"],"is_corresponding":false,"raw_author_name":"Jun Takagi","raw_affiliation_strings":["Department of Chemistry, Yale University, P.O. Box 208107, New Haven, Connecticut 06520-8107","Division of Molecular Chemistry, Graduate School of Engineering, Hokkaido University, Sapporo 060-8628, Japan"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Department of Chemistry, Yale University, P.O. Box 208107, New Haven, Connecticut 06520-8107","institution_ids":["https://openalex.org/I32971472"]},{"raw_affiliation_string":"Division of Molecular Chemistry, Graduate School of Engineering, Hokkaido University, Sapporo 060-8628, Japan","institution_ids":["https://openalex.org/I205349734"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5056440418","display_name":"Kousaku Ishida","orcid":null,"observed_orcids":[]},"institutions":[{"id":"https://openalex.org/I205349734","display_name":"Hokkaido University","ror":"https://ror.org/02e16g702","country_code":"JP","type":"education","lineage":["https://openalex.org/I205349734"]},{"id":"https://openalex.org/I32971472","display_name":"Yale University","ror":"https://ror.org/03v76x132","country_code":"US","type":"education","lineage":["https://openalex.org/I32971472"]}],"countries":["JP","US"],"is_corresponding":false,"raw_author_name":"Kousaku Ishida","raw_affiliation_strings":["Department of Chemistry, Yale University, P.O. Box 208107, New Haven, Connecticut 06520-8107","Division of Molecular Chemistry, Graduate School of Engineering, Hokkaido University, Sapporo 060-8628, Japan"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Department of Chemistry, Yale University, P.O. Box 208107, New Haven, Connecticut 06520-8107","institution_ids":["https://openalex.org/I32971472"]},{"raw_affiliation_string":"Division of Molecular Chemistry, Graduate School of Engineering, Hokkaido University, Sapporo 060-8628, Japan","institution_ids":["https://openalex.org/I205349734"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5037653616","display_name":"Norio Miyaura","orcid":null,"observed_orcids":[]},"institutions":[{"id":"https://openalex.org/I205349734","display_name":"Hokkaido University","ror":"https://ror.org/02e16g702","country_code":"JP","type":"education","lineage":["https://openalex.org/I205349734"]},{"id":"https://openalex.org/I32971472","display_name":"Yale University","ror":"https://ror.org/03v76x132","country_code":"US","type":"education","lineage":["https://openalex.org/I32971472"]}],"countries":["JP","US"],"is_corresponding":false,"raw_author_name":"Norio Miyaura","raw_affiliation_strings":["Department of Chemistry, Yale University, P.O. Box 208107, New Haven, Connecticut 06520-8107","Division of Molecular Chemistry, Graduate School of Engineering, Hokkaido University, Sapporo 060-8628, Japan"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Department of Chemistry, Yale University, P.O. Box 208107, New Haven, Connecticut 06520-8107","institution_ids":["https://openalex.org/I32971472"]},{"raw_affiliation_string":"Division of Molecular Chemistry, Graduate School of Engineering, Hokkaido University, Sapporo 060-8628, Japan","institution_ids":["https://openalex.org/I205349734"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5058373920","display_name":"Natia R. Anastasi","orcid":"https://orcid.org/0000-0003-4345-0688","observed_orcids":["https://orcid.org/0000-0003-4345-0688"]},"institutions":[{"id":"https://openalex.org/I205349734","display_name":"Hokkaido University","ror":"https://ror.org/02e16g702","country_code":"JP","type":"education","lineage":["https://openalex.org/I205349734"]},{"id":"https://openalex.org/I32971472","display_name":"Yale University","ror":"https://ror.org/03v76x132","country_code":"US","type":"education","lineage":["https://openalex.org/I32971472"]}],"countries":["JP","US"],"is_corresponding":false,"raw_author_name":"Natia R. Anastasi","raw_affiliation_strings":["Department of Chemistry, Yale University, P.O. Box 208107, New Haven, Connecticut 06520-8107","Division of Molecular Chemistry, Graduate School of Engineering, Hokkaido University, Sapporo 060-8628, Japan"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Department of Chemistry, Yale University, P.O. Box 208107, New Haven, Connecticut 06520-8107","institution_ids":["https://openalex.org/I32971472"]},{"raw_affiliation_string":"Division of Molecular Chemistry, Graduate School of Engineering, Hokkaido University, Sapporo 060-8628, Japan","institution_ids":["https://openalex.org/I205349734"]}]},{"author_position":"last","author":{"id":"https://openalex.org/A5088865204","display_name":"John F. Hartwig","orcid":"https://orcid.org/0000-0002-4157-468X","observed_orcids":["https://orcid.org/0000-0002-4157-468X"]},"institutions":[{"id":"https://openalex.org/I205349734","display_name":"Hokkaido University","ror":"https://ror.org/02e16g702","country_code":"JP","type":"education","lineage":["https://openalex.org/I205349734"]},{"id":"https://openalex.org/I32971472","display_name":"Yale University","ror":"https://ror.org/03v76x132","country_code":"US","type":"education","lineage":["https://openalex.org/I32971472"]}],"countries":["JP","US"],"is_corresponding":false,"raw_author_name":"John F. Hartwig","raw_affiliation_strings":["Department of Chemistry, Yale University, P.O. Box 208107, New Haven, Connecticut 06520-8107","Division of Molecular Chemistry, Graduate School of Engineering, Hokkaido University, Sapporo 060-8628, Japan"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Department of Chemistry, Yale University, P.O. Box 208107, New Haven, Connecticut 06520-8107","institution_ids":["https://openalex.org/I32971472"]},{"raw_affiliation_string":"Division of Molecular Chemistry, Graduate School of Engineering, Hokkaido University, Sapporo 060-8628, Japan","institution_ids":["https://openalex.org/I205349734"]}]}],"institutions":[],"countries_distinct_count":2,"institutions_distinct_count":2,"corresponding_author_ids":[],"corresponding_institution_ids":[],"apc_list":{"value":4500,"currency":"USD","value_usd":4500},"apc_paid":null,"fwci":13.6526,"has_fulltext":false,"cited_by_count":1158,"citation_normalized_percentile":{"value":0.99679412,"is_in_top_1_percent":true,"is_in_top_10_percent":true},"cited_by_percentile_year":{"min":99,"max":100},"biblio":{"volume":"124","issue":"3","first_page":"390","last_page":"391"},"is_retracted":false,"is_paratext":false,"is_xpac":false,"primary_topic":{"id":"https://openalex.org/T10548","display_name":"Catalytic Cross-Coupling Reactions","score":0.5981000065803528,"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/T10548","display_name":"Catalytic Cross-Coupling Reactions","score":0.5981000065803528,"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":0.2930000126361847,"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":0.05290000140666962,"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/iridium-catalysis","display_name":"iridium catalysis","score":0.9819999933242798},{"id":"https://openalex.org/keywords/bipyridine-ligands","display_name":"bipyridine ligands","score":0.8790000081062317},{"id":"https://openalex.org/keywords/room-temperature-reaction","display_name":"room temperature reaction","score":0.5609999895095825},{"id":"https://openalex.org/keywords/unactivated-arenes","display_name":"unactivated arenes","score":0.7440000176429749},{"id":"https://openalex.org/keywords/reaction-mechanism","display_name":"reaction mechanism","score":0.4620000123977661}],"concepts":[{"id":"https://openalex.org/C2776413204","wikidata":"https://www.wikidata.org/wiki/Q17113001","display_name":"Borylation","level":4,"score":0.9935449361801147},{"id":"https://openalex.org/C185592680","wikidata":"https://www.wikidata.org/wiki/Q2329","display_name":"Chemistry","level":0,"score":0.9671618938446045},{"id":"https://openalex.org/C528581852","wikidata":"https://www.wikidata.org/wiki/Q877","display_name":"Iridium","level":3,"score":0.7691102027893066},{"id":"https://openalex.org/C161790260","wikidata":"https://www.wikidata.org/wiki/Q82264","display_name":"Catalysis","level":2,"score":0.689893901348114},{"id":"https://openalex.org/C40875361","wikidata":"https://www.wikidata.org/wiki/Q2356542","display_name":"Reagent","level":2,"score":0.6786714196205139},{"id":"https://openalex.org/C2781076698","wikidata":"https://www.wikidata.org/wiki/Q718074","display_name":"Aryl","level":3,"score":0.6220611929893494},{"id":"https://openalex.org/C21951064","wikidata":"https://www.wikidata.org/wiki/Q899212","display_name":"Combinatorial chemistry","level":1,"score":0.4816547930240631},{"id":"https://openalex.org/C73969872","wikidata":"https://www.wikidata.org/wiki/Q899698","display_name":"Turnover number","level":3,"score":0.4540083110332489},{"id":"https://openalex.org/C155647269","wikidata":"https://www.wikidata.org/wiki/Q243455","display_name":"Medicinal chemistry","level":1,"score":0.3996764123439789},{"id":"https://openalex.org/C75473681","wikidata":"https://www.wikidata.org/wiki/Q188651","display_name":"Photochemistry","level":1,"score":0.35026249289512634},{"id":"https://openalex.org/C178790620","wikidata":"https://www.wikidata.org/wiki/Q11351","display_name":"Organic chemistry","level":1,"score":0.3478929400444031},{"id":"https://openalex.org/C2780263894","wikidata":"https://www.wikidata.org/wiki/Q335268","display_name":"Alkyl","level":2,"score":0.0}],"mesh":[],"locations_count":2,"locations":[{"id":"doi:10.1021/ja0173019","doi":"https://doi.org/10.1021/ja0173019","is_oa":false,"landing_page_url":"https://doi.org/10.1021/ja0173019","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:11792205","doi":null,"is_oa":false,"landing_page_url":"https://pubmed.ncbi.nlm.nih.gov/11792205","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":[],"funders":[],"has_content":{"pdf":false,"grobid_xml":false},"content_urls":null,"referenced_works_count":23,"referenced_works":["https://openalex.org/W603998475","https://openalex.org/W1969676465","https://openalex.org/W1972730799","https://openalex.org/W1978890358","https://openalex.org/W1980290845","https://openalex.org/W1983533257","https://openalex.org/W1990880086","https://openalex.org/W2010063460","https://openalex.org/W2017033936","https://openalex.org/W2039479509","https://openalex.org/W2040299058","https://openalex.org/W2045444647","https://openalex.org/W2057856989","https://openalex.org/W2064308089","https://openalex.org/W2074664376","https://openalex.org/W2077685191","https://openalex.org/W2095426967","https://openalex.org/W2110940252","https://openalex.org/W2119537222","https://openalex.org/W2133502386","https://openalex.org/W2150411284","https://openalex.org/W4253144454","https://openalex.org/W4285719527"],"related_works":["https://openalex.org/W2952738478","https://openalex.org/W2169142393","https://openalex.org/W2025195522","https://openalex.org/W1997453632","https://openalex.org/W2950271871","https://openalex.org/W2766182862","https://openalex.org/W2735884041","https://openalex.org/W4220881612","https://openalex.org/W1974939331","https://openalex.org/W2179910071"],"abstract_inverted_index":{"The":[0,47,64,77],"borylation":[1,31],"of":[2,8,32,66,108,111],"arenes":[3,33,40],"leads":[4],"to":[5,127],"the":[6,30,51,99],"formation":[7],"synthetically":[9],"versatile":[10],"products":[11],"from":[12],"unactivated":[13],"arene":[14,62],"reagents.":[15],"We":[16],"report":[17],"that":[18,98],"Ir(I)":[19],"precursors":[20],"in":[21,27,132],"conjunction":[22],"with":[23],"bipyridine":[24],"ligands":[25],"catalyze":[26],"high":[28,87,133],"yields":[29],"under":[34],"mild":[35],"conditions.":[36],"These":[37],"reactions":[38,100],"encompase":[39],"bearing":[41],"both":[42],"electron-withdrawing":[43],"and":[44,68,118],"electron-donating":[45],"substituents.":[46],"temperatures":[48],"required":[49],"for":[50,60,72,90],"transformation":[52],"are":[53],"much":[54],"lower":[55],"than":[56],"those":[57],"previously":[58],"reported":[59],"direct":[61],"borylation.":[63],"combination":[65],"[Ir(COE)2Cl]2":[67],"(4,4-di-t-butyl)bipyridine":[69],"even":[70],"allows":[71],"reaction":[73],"at":[74,81,124],"room":[75,125],"temperature.":[76],"same":[78],"catalyst":[79],"system":[80],"100":[82],"degrees":[83],"C":[84],"provides":[85],"remarkably":[86],"turnover":[88],"numbers":[89],"a":[91],"hydrocarbon":[92],"functionalization":[93],"process.":[94],"Mechanistic":[95],"studies":[96],"show":[97],"involve":[101],"uncommon,":[102],"Ir(II)":[103],"tris-boryl":[104],"complexes.":[105],"An":[106],"example":[107],"this":[109],"type":[110],"complex":[112],"ligated":[113],"by":[114],"di-t-butylbipyridine":[115],"was":[116],"isolated":[117],"structurally":[119],"characterized.":[120],"It":[121],"reacted":[122],"rapidly":[123],"temperature":[126],"produce":[128],"aryl":[129],"boronate":[130],"esters":[131],"yields.":[134]},"counts_by_year":[{"year":2026,"cited_by_count":27},{"year":2025,"cited_by_count":49},{"year":2024,"cited_by_count":55},{"year":2023,"cited_by_count":44},{"year":2022,"cited_by_count":58},{"year":2021,"cited_by_count":72},{"year":2020,"cited_by_count":71},{"year":2019,"cited_by_count":65},{"year":2018,"cited_by_count":59},{"year":2017,"cited_by_count":67},{"year":2016,"cited_by_count":66},{"year":2015,"cited_by_count":75},{"year":2014,"cited_by_count":57},{"year":2013,"cited_by_count":56},{"year":2012,"cited_by_count":50}],"updated_date":"2026-11-12T12:28:57.059296","created_date":"2016-06-24T00:00:00"}