{"id":"https://openalex.org/W2952419475","doi":"https://doi.org/10.1021/ja056076i","title":"Palladium-Catalyzed Intermolecular \u03b1-Arylation of Zinc Amide Enolates under Mild Conditions","display_name":"Palladium-Catalyzed Intermolecular \u03b1-Arylation of Zinc Amide Enolates under Mild Conditions","publication_year":2006,"publication_date":"2006-03-25","ids":{"openalex":"https://openalex.org/W2952419475","doi":"https://doi.org/10.1021/ja056076i","mag":"2952419475","pmid":"https://pubmed.ncbi.nlm.nih.gov/16608331"},"language":"en","primary_location":{"id":"doi:10.1021/ja056076i","doi":"https://doi.org/10.1021/ja056076i","is_oa":false,"landing_page_url":"https://doi.org/10.1021/ja056076i","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/A5003609998","display_name":"Takuo Hama","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":"Takuo Hama","raw_affiliation_strings":["Contribution from the Department of Chemistry, Yale University, P.O. Box 208107, New Haven, Connecticut 06520-8107","Department of Chemistry, Yale University, P.O. Box 208107, New Haven, Connecticut 06520 8107, USA"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Contribution from the Department of Chemistry, Yale University, P.O. Box 208107, New Haven, Connecticut 06520-8107","institution_ids":["https://openalex.org/I32971472"]},{"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/A5001583157","display_name":"Darcy A. Culkin","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":"Darcy A. Culkin","raw_affiliation_strings":["Contribution from the Department of Chemistry, Yale University, P.O. Box 208107, New Haven, Connecticut 06520-8107"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Contribution from the Department of Chemistry, Yale University, P.O. Box 208107, New Haven, Connecticut 06520-8107","institution_ids":["https://openalex.org/I32971472"]}]},{"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/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":"John F. Hartwig","raw_affiliation_strings":["Contribution from the Department of Chemistry, Yale University, P.O. Box 208107, New Haven, Connecticut 06520-8107"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Contribution from the Department of Chemistry, Yale University, P.O. Box 208107, New Haven, Connecticut 06520-8107","institution_ids":["https://openalex.org/I32971472"]}]}],"institutions":[],"countries_distinct_count":1,"institutions_distinct_count":1,"corresponding_author_ids":[],"corresponding_institution_ids":["https://openalex.org/I32971472"],"apc_list":{"value":4500,"currency":"USD","value_usd":4500},"apc_paid":null,"fwci":11.2132,"has_fulltext":false,"cited_by_count":202,"citation_normalized_percentile":{"value":0.99239071,"is_in_top_1_percent":true,"is_in_top_10_percent":true},"cited_by_percentile_year":{"min":89,"max":100},"biblio":{"volume":"128","issue":"15","first_page":"4976","last_page":"4985"},"is_retracted":false,"is_paratext":false,"is_xpac":false,"primary_topic":{"id":"https://openalex.org/T10548","display_name":"Catalytic Cross-Coupling Reactions","score":0.9976000189781189,"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":0.9976000189781189,"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":0.0015999999595806003,"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":9.999999747378752e-05,"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/palladium-catalysis","display_name":"palladium catalysis","score":0.984000027179718},{"id":"https://openalex.org/keywords/reformatsky-reagent","display_name":"Reformatsky reagent","score":0.8510000109672546},{"id":"https://openalex.org/keywords/aryl-bromides","display_name":"aryl bromides","score":0.7239999771118164},{"id":"https://openalex.org/keywords/vinyl-bromides","display_name":"vinyl bromides","score":0.9649999737739563},{"id":"https://openalex.org/keywords/vinylation","display_name":"vinylation","score":0.6489999890327454},{"id":"https://openalex.org/keywords/bromopyridines","display_name":"bromopyridines","score":0.753000020980835},{"id":"https://openalex.org/keywords/room-temperature-reaction","display_name":"room temperature reaction","score":0.4950000047683716}],"concepts":[{"id":"https://openalex.org/C185592680","wikidata":"https://www.wikidata.org/wiki/Q2329","display_name":"Chemistry","level":0,"score":0.9708293676376343},{"id":"https://openalex.org/C535196362","wikidata":"https://www.wikidata.org/wiki/Q758","display_name":"Zinc","level":2,"score":0.7786011695861816},{"id":"https://openalex.org/C2781076698","wikidata":"https://www.wikidata.org/wiki/Q718074","display_name":"Aryl","level":3,"score":0.6804308295249939},{"id":"https://openalex.org/C502130503","wikidata":"https://www.wikidata.org/wiki/Q1089","display_name":"Palladium","level":3,"score":0.6589547991752625},{"id":"https://openalex.org/C2778439535","wikidata":"https://www.wikidata.org/wiki/Q188777","display_name":"Amide","level":2,"score":0.653490424156189},{"id":"https://openalex.org/C161790260","wikidata":"https://www.wikidata.org/wiki/Q82264","display_name":"Catalysis","level":2,"score":0.6461718082427979},{"id":"https://openalex.org/C40875361","wikidata":"https://www.wikidata.org/wiki/Q2356542","display_name":"Reagent","level":2,"score":0.6010308861732483},{"id":"https://openalex.org/C178790620","wikidata":"https://www.wikidata.org/wiki/Q11351","display_name":"Organic chemistry","level":1,"score":0.5326312184333801},{"id":"https://openalex.org/C171560689","wikidata":"https://www.wikidata.org/wiki/Q193086","display_name":"Halide","level":2,"score":0.4312204122543335},{"id":"https://openalex.org/C155647269","wikidata":"https://www.wikidata.org/wiki/Q243455","display_name":"Medicinal chemistry","level":1,"score":0.363718181848526},{"id":"https://openalex.org/C2780263894","wikidata":"https://www.wikidata.org/wiki/Q335268","display_name":"Alkyl","level":2,"score":0.0}],"mesh":[{"descriptor_ui":"D000577","descriptor_name":"Amides","qualifier_ui":"Q000737","qualifier_name":"chemistry","is_major_topic":true},{"descriptor_ui":"D001555","descriptor_name":"Benzene Derivatives","qualifier_ui":"Q000138","qualifier_name":"chemical synthesis","is_major_topic":true},{"descriptor_ui":"D001555","descriptor_name":"Benzene Derivatives","qualifier_ui":"Q000737","qualifier_name":"chemistry","is_major_topic":false},{"descriptor_ui":"D002384","descriptor_name":"Catalysis","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D006842","descriptor_name":"Hydrocarbons, Brominated","qualifier_ui":"Q000737","qualifier_name":"chemistry","is_major_topic":false},{"descriptor_ui":"D007659","descriptor_name":"Ketones","qualifier_ui":"Q000138","qualifier_name":"chemical synthesis","is_major_topic":true},{"descriptor_ui":"D007659","descriptor_name":"Ketones","qualifier_ui":"Q000737","qualifier_name":"chemistry","is_major_topic":false},{"descriptor_ui":"D009025","descriptor_name":"Morpholines","qualifier_ui":"Q000737","qualifier_name":"chemistry","is_major_topic":false},{"descriptor_ui":"D009942","descriptor_name":"Organometallic Compounds","qualifier_ui":"Q000737","qualifier_name":"chemistry","is_major_topic":false},{"descriptor_ui":"D010165","descriptor_name":"Palladium","qualifier_ui":"Q000737","qualifier_name":"chemistry","is_major_topic":false},{"descriptor_ui":"D014753","descriptor_name":"Vinyl Compounds","qualifier_ui":"Q000737","qualifier_name":"chemistry","is_major_topic":false},{"descriptor_ui":"D015032","descriptor_name":"Zinc","qualifier_ui":"Q000737","qualifier_name":"chemistry","is_major_topic":true},{"descriptor_ui":"D018020","descriptor_name":"Lithium Compounds","qualifier_ui":"Q000737","qualifier_name":"chemistry","is_major_topic":false}],"locations_count":2,"locations":[{"id":"doi:10.1021/ja056076i","doi":"https://doi.org/10.1021/ja056076i","is_oa":false,"landing_page_url":"https://doi.org/10.1021/ja056076i","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:16608331","doi":null,"is_oa":false,"landing_page_url":"https://pubmed.ncbi.nlm.nih.gov/16608331","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/G1921871789","display_name":null,"funder_award_id":"GM 58108","funder_id":"https://openalex.org/F4320337354","funder_display_name":"National Institute of General Medical Sciences"},{"id":"https://openalex.org/G6735034421","display_name":"Mechanism and Rational Development of Catalytic Carbon-Carbon Bond-Forming Reacti","funder_award_id":"R01GM058108","funder_id":"https://openalex.org/F4320337354","funder_display_name":"National Institute of General Medical Sciences"}],"funders":[{"id":"https://openalex.org/F4320337354","display_name":"National Institute of General Medical Sciences","ror":"https://ror.org/04q48ey07"}],"has_content":{"grobid_xml":false,"pdf":false},"content_urls":null,"referenced_works_count":97,"referenced_works":["https://openalex.org/W1863307104","https://openalex.org/W1965166604","https://openalex.org/W1965783160","https://openalex.org/W1966004885","https://openalex.org/W1966352321","https://openalex.org/W1969106484","https://openalex.org/W1969533214","https://openalex.org/W1972611478","https://openalex.org/W1973018553","https://openalex.org/W1974328891","https://openalex.org/W1979489398","https://openalex.org/W1980419092","https://openalex.org/W1980755782","https://openalex.org/W1982298201","https://openalex.org/W1983763086","https://openalex.org/W1986391261","https://openalex.org/W1986831013","https://openalex.org/W1987538243","https://openalex.org/W1989288103","https://openalex.org/W1990701326","https://openalex.org/W1991230641","https://openalex.org/W1991394589","https://openalex.org/W1991608816","https://openalex.org/W1994153602","https://openalex.org/W1995504817","https://openalex.org/W1995734593","https://openalex.org/W1998750278","https://openalex.org/W2001889144","https://openalex.org/W2003296412","https://openalex.org/W2003857865","https://openalex.org/W2005692012","https://openalex.org/W2006559191","https://openalex.org/W2008394094","https://openalex.org/W2011883651","https://openalex.org/W2013889067","https://openalex.org/W2016076296","https://openalex.org/W2016200600","https://openalex.org/W2018241366","https://openalex.org/W2028778764","https://openalex.org/W2039271538","https://openalex.org/W2039738701","https://openalex.org/W2044580907","https://openalex.org/W2047798970","https://openalex.org/W2048126999","https://openalex.org/W2049387887","https://openalex.org/W2051218898","https://openalex.org/W2053502743","https://openalex.org/W2053932169","https://openalex.org/W2054411193","https://openalex.org/W2056650671","https://openalex.org/W2056859548","https://openalex.org/W2059981246","https://openalex.org/W2061343703","https://openalex.org/W2062353246","https://openalex.org/W2068961891","https://openalex.org/W2071612993","https://openalex.org/W2075048800","https://openalex.org/W2075617267","https://openalex.org/W2077228883","https://openalex.org/W2080925478","https://openalex.org/W2084992960","https://openalex.org/W2085080968","https://openalex.org/W2085925544","https://openalex.org/W2086930673","https://openalex.org/W2087565617","https://openalex.org/W2094871139","https://openalex.org/W2095356415","https://openalex.org/W2098260753","https://openalex.org/W2101904590","https://openalex.org/W2102330027","https://openalex.org/W2111907823","https://openalex.org/W2113178062","https://openalex.org/W2119016897","https://openalex.org/W2131759961","https://openalex.org/W2145790731","https://openalex.org/W2148177192","https://openalex.org/W2149476429","https://openalex.org/W2150805674","https://openalex.org/W2150823185","https://openalex.org/W2151640189","https://openalex.org/W2164930732","https://openalex.org/W2167657940","https://openalex.org/W2172556925","https://openalex.org/W2333527022","https://openalex.org/W2950110483","https://openalex.org/W2950481131","https://openalex.org/W2950541942","https://openalex.org/W2950637581","https://openalex.org/W2950968159","https://openalex.org/W2951670733","https://openalex.org/W2951952237","https://openalex.org/W2952007241","https://openalex.org/W2952252703","https://openalex.org/W2952286917","https://openalex.org/W2952530370","https://openalex.org/W2953014944","https://openalex.org/W4233748396"],"related_works":["https://openalex.org/W2055975983","https://openalex.org/W2094049803","https://openalex.org/W2016200600","https://openalex.org/W2951835106","https://openalex.org/W4406188527","https://openalex.org/W2951670733","https://openalex.org/W2016036317","https://openalex.org/W2086930673","https://openalex.org/W2013094949","https://openalex.org/W2949806362"],"abstract_inverted_index":{"The":[0,34,91,135],"intermolecular":[1],"alpha-arylation":[2],"and":[3,13,60,113,133],"vinylation":[4],"of":[5,10,19,24,28,36,69,76,80,88,127,137,140],"amides":[6,20,70,141],"by":[7,65],"palladium-catalyzed":[8],"coupling":[9],"aryl":[11,37],"bromides":[12,15],"vinyl":[14],"with":[16,43,51,61,71,101,114,122,144],"zinc":[17,29,62,72,77,138],"enolates":[18,30,63,68,139],"is":[21],"reported.":[22],"Reactions":[23],"three":[25],"different":[26],"types":[27],"have":[31],"been":[32,120],"developed.":[33],"reactions":[35,92],"halides":[38],"occur":[39,93],"in":[40,55],"high":[41],"yields":[42],"isolated":[44],"Reformatsky":[45,52],"reagents":[46,53],"generated":[47,54,64],"from":[48,57],"alpha-bromo":[49,58],"amides,":[50,59,124],"situ":[56],"quenching":[66],"lithium":[67],"chloride.":[73],"This":[74],"use":[75],"enolates,":[78,83],"instead":[79],"alkali":[81],"metal":[82],"greatly":[84],"expands":[85],"the":[86,117,125,147,153],"scope":[87],"amide":[89],"arylation.":[90],"at":[94],"room":[95],"temperature":[96],"or":[97,110,152],"70":[98],"degrees":[99],"C":[100],"bromoarenes":[102],"containing":[103],"cyano,":[104],"nitro,":[105],"ester,":[106],"keto,":[107],"fluoro,":[108],"hydroxyl,":[109],"amino":[111],"functionality":[112],"bromopyridines.":[115],"Moreover,":[116],"reaction":[118],"has":[119],"developed":[121],"morpholine":[123],"products":[126],"which":[128],"are":[129],"precursors":[130],"to":[131],"ketones":[132],"aldehydes.":[134],"arylation":[136],"was":[142],"conducted":[143],"catalysts":[145],"bearing":[146],"hindered":[148],"pentaphenylferrocenyl":[149],"di-tert-butylphosphine":[150],"(Q-phos)":[151],"highly":[154],"reactive,":[155],"dimeric,":[156],"Pd(I)":[157],"complex":[158],"[[P(t-Bu)3]PdBr]2.":[159]},"counts_by_year":[{"year":2026,"cited_by_count":3},{"year":2025,"cited_by_count":3},{"year":2024,"cited_by_count":7},{"year":2023,"cited_by_count":1},{"year":2022,"cited_by_count":5},{"year":2021,"cited_by_count":8},{"year":2020,"cited_by_count":9},{"year":2019,"cited_by_count":7},{"year":2018,"cited_by_count":6},{"year":2017,"cited_by_count":12},{"year":2016,"cited_by_count":5},{"year":2015,"cited_by_count":12},{"year":2014,"cited_by_count":22},{"year":2013,"cited_by_count":16},{"year":2012,"cited_by_count":6}],"updated_date":"2026-10-31T12:09:11.096373","created_date":"2019-06-27T00:00:00"}
