{"id":"https://openalex.org/W4394728071","doi":"https://doi.org/10.1021/acscatal.4c00648","title":"Nickel-Based Catalysts for the Selective Monoarylation of Dichloropyridines: Ligand Effects and Mechanistic Insights","display_name":"Nickel-Based Catalysts for the Selective Monoarylation of Dichloropyridines: Ligand Effects and Mechanistic Insights","publication_year":2024,"publication_date":"2024-04-11","ids":{"openalex":"https://openalex.org/W4394728071","doi":"https://doi.org/10.1021/acscatal.4c00648","pmid":"https://pubmed.ncbi.nlm.nih.gov/38911467","pmcid":"https://www.ncbi.nlm.nih.gov/pmc/articles/11192541"},"language":"en","primary_location":{"id":"doi:10.1021/acscatal.4c00648","doi":"https://doi.org/10.1021/acscatal.4c00648","is_oa":false,"landing_page_url":"https://doi.org/10.1021/acscatal.4c00648","pdf_url":null,"source":{"id":"https://openalex.org/S37391459","display_name":"ACS Catalysis","issn_l":"2155-5435","issn":["2155-5435"],"is_oa":false,"is_in_doaj":false,"is_core":true,"listed_in":["cwts-core","dongbi-a","jufo-3","ki-jl-2","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":"ACS Catalysis","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://pmc.ncbi.nlm.nih.gov/articles/PMC11192541/pdf/nihms-2000308.pdf","any_repository_has_fulltext":true},"authorships":[{"author_position":"first","author":{"id":"https://openalex.org/A5057744441","display_name":"Geraldo Duran-Camacho","orcid":"https://orcid.org/0000-0001-9982-6280","observed_orcids":["https://orcid.org/0000-0001-9982-6280"]},"institutions":[{"id":"https://openalex.org/I27837315","display_name":"University of Michigan","ror":"https://ror.org/00jmfr291","country_code":"US","type":"education","lineage":["https://openalex.org/I27837315"]}],"countries":["US"],"is_corresponding":false,"raw_author_name":"Geraldo Duran-Camacho","raw_affiliation_strings":["Department of Chemistry, University of Michigan, 930 North Avenue, Ann Arbor, Michigan 48104, United States"],"raw_orcid":"https://orcid.org/0000-0001-9982-6280","affiliations":[{"raw_affiliation_string":"Department of Chemistry, University of Michigan, 930 North Avenue, Ann Arbor, Michigan 48104, United States","institution_ids":["https://openalex.org/I27837315"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5003455653","display_name":"Douglas C. Bland","orcid":null,"observed_orcids":[]},"institutions":[{"id":"https://openalex.org/I4210121787","display_name":"Corteva (United States)","ror":"https://ror.org/02pm1jf23","country_code":"US","type":"company","lineage":["https://openalex.org/I4210121787"]}],"countries":["US"],"is_corresponding":false,"raw_author_name":"Douglas C. Bland","raw_affiliation_strings":["Product & Process Technology R&D, Corteva Agriscience, 9330 Zionsville Road, Indianapolis, Indiana 46268, United States"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Product & Process Technology R&D, Corteva Agriscience, 9330 Zionsville Road, Indianapolis, Indiana 46268, United States","institution_ids":["https://openalex.org/I4210121787"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5101899801","display_name":"Fangzheng Li","orcid":"https://orcid.org/0000-0002-7570-7938","observed_orcids":["https://orcid.org/0000-0002-7570-7938"]},"institutions":[{"id":"https://openalex.org/I4210121787","display_name":"Corteva (United States)","ror":"https://ror.org/02pm1jf23","country_code":"US","type":"company","lineage":["https://openalex.org/I4210121787"]}],"countries":["US"],"is_corresponding":false,"raw_author_name":"Fangzheng Li","raw_affiliation_strings":["Product & Process Technology R&D, Corteva Agriscience, 9330 Zionsville Road, Indianapolis, Indiana 46268, United States"],"raw_orcid":"https://orcid.org/0000-0002-7570-7938","affiliations":[{"raw_affiliation_string":"Product & Process Technology R&D, Corteva Agriscience, 9330 Zionsville Road, Indianapolis, Indiana 46268, United States","institution_ids":["https://openalex.org/I4210121787"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5087575581","display_name":"Sharon R. Neufeldt","orcid":"https://orcid.org/0000-0001-7995-3995","observed_orcids":["https://orcid.org/0000-0001-7995-3995"]},"institutions":[{"id":"https://openalex.org/I23732399","display_name":"Montana State University","ror":"https://ror.org/02w0trx84","country_code":"US","type":"education","lineage":["https://openalex.org/I23732399","https://openalex.org/I4210126032"]}],"countries":["US"],"is_corresponding":true,"raw_author_name":"Sharon R. Neufeldt","raw_affiliation_strings":["Department of Chemistry and Biochemistry, Montana State University, Bozeman, Montana 59717, United States"],"raw_orcid":"https://orcid.org/0000-0001-7995-3995","affiliations":[{"raw_affiliation_string":"Department of Chemistry and Biochemistry, Montana State University, Bozeman, Montana 59717, United States","institution_ids":["https://openalex.org/I23732399"]}]},{"author_position":"last","author":{"id":"https://openalex.org/A5028785945","display_name":"Melanie Sarah Sanford","orcid":"https://orcid.org/0000-0001-9342-9436","observed_orcids":["https://orcid.org/0000-0001-9342-9436"]},"institutions":[{"id":"https://openalex.org/I27837315","display_name":"University of Michigan","ror":"https://ror.org/00jmfr291","country_code":"US","type":"education","lineage":["https://openalex.org/I27837315"]}],"countries":["US"],"is_corresponding":true,"raw_author_name":"Melanie S. Sanford","raw_affiliation_strings":["Department of Chemistry, University of Michigan, 930 North Avenue, Ann Arbor, Michigan 48104, United States"],"raw_orcid":"https://orcid.org/0000-0001-9342-9436","affiliations":[{"raw_affiliation_string":"Department of Chemistry, University of Michigan, 930 North Avenue, Ann Arbor, Michigan 48104, United States","institution_ids":["https://openalex.org/I27837315"]}]}],"institutions":[],"countries_distinct_count":1,"institutions_distinct_count":3,"corresponding_author_ids":["https://openalex.org/A5028785945","https://openalex.org/A5087575581"],"corresponding_institution_ids":["https://openalex.org/I23732399","https://openalex.org/I27837315"],"apc_list":{"value":4500,"currency":"USD","value_usd":4500},"apc_paid":null,"fwci":1.2368,"has_fulltext":true,"cited_by_count":9,"citation_normalized_percentile":{"value":0.73612754,"is_in_top_1_percent":false,"is_in_top_10_percent":false},"cited_by_percentile_year":{"min":93,"max":98},"biblio":{"volume":"14","issue":"9","first_page":"6404","last_page":"6412"},"is_retracted":false,"is_paratext":false,"is_xpac":false,"primary_topic":{"id":"https://openalex.org/T10548","display_name":"Catalytic Cross-Coupling Reactions","score":1.0,"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":1.0,"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":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"}},{"id":"https://openalex.org/T10354","display_name":"Catalytic C\u2013H Functionalization Methods","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/nickel-catalysis","display_name":"nickel catalysis","score":0.8629999756813049},{"id":"https://openalex.org/keywords/suzuki-miyaura-coupling","display_name":"Suzuki coupling","score":0.8379999995231628},{"id":"https://openalex.org/keywords/monoarylation","display_name":"monoarylation","score":0.8410000205039978},{"id":"https://openalex.org/keywords/phosphine-ligands","display_name":"phosphine ligands","score":0.8529999852180481},{"id":"https://openalex.org/keywords/tolman-cone-angle","display_name":"Tolman cone angle","score":0.8489999771118164},{"id":"https://openalex.org/keywords/ligand-exchange","display_name":"ligand exchange","score":0.6819999814033508},{"id":"https://openalex.org/keywords/solvent-effects","display_name":"solvent effects","score":0.7360000014305115},{"id":"https://openalex.org/keywords/arylboronic-acids","display_name":"arylboronic acids","score":0.828000009059906},{"id":"https://openalex.org/keywords/oligomerization","display_name":"oligomerization","score":0.5699999928474426}],"concepts":[{"id":"https://openalex.org/C161790260","wikidata":"https://www.wikidata.org/wiki/Q82264","display_name":"Catalysis","level":2,"score":0.7766492366790771},{"id":"https://openalex.org/C504270822","wikidata":"https://www.wikidata.org/wiki/Q744","display_name":"Nickel","level":2,"score":0.7241683006286621},{"id":"https://openalex.org/C116569031","wikidata":"https://www.wikidata.org/wiki/Q899107","display_name":"Ligand (biochemistry)","level":3,"score":0.5787025690078735},{"id":"https://openalex.org/C185592680","wikidata":"https://www.wikidata.org/wiki/Q2329","display_name":"Chemistry","level":0,"score":0.5345335006713867},{"id":"https://openalex.org/C21951064","wikidata":"https://www.wikidata.org/wiki/Q899212","display_name":"Combinatorial chemistry","level":1,"score":0.3949849009513855},{"id":"https://openalex.org/C178790620","wikidata":"https://www.wikidata.org/wiki/Q11351","display_name":"Organic chemistry","level":1,"score":0.1985466480255127},{"id":"https://openalex.org/C55493867","wikidata":"https://www.wikidata.org/wiki/Q7094","display_name":"Biochemistry","level":1,"score":0.06821680068969727},{"id":"https://openalex.org/C170493617","wikidata":"https://www.wikidata.org/wiki/Q208467","display_name":"Receptor","level":2,"score":0.0}],"mesh":[],"locations_count":4,"locations":[{"id":"doi:10.1021/acscatal.4c00648","doi":"https://doi.org/10.1021/acscatal.4c00648","is_oa":false,"landing_page_url":"https://doi.org/10.1021/acscatal.4c00648","pdf_url":null,"source":{"id":"https://openalex.org/S37391459","display_name":"ACS Catalysis","issn_l":"2155-5435","issn":["2155-5435"],"is_oa":false,"is_in_doaj":false,"is_core":true,"listed_in":["cwts-core","dongbi-a","jufo-3","ki-jl-2","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":"ACS Catalysis","raw_type":"journal-article"},{"id":"pmid:38911467","doi":null,"is_oa":false,"landing_page_url":"https://pubmed.ncbi.nlm.nih.gov/38911467","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":"ACS catalysis","raw_type":"Journal Article"},{"id":"pmh:oai:pubmedcentral.nih.gov:11192541","doi":null,"is_oa":true,"landing_page_url":"https://www.ncbi.nlm.nih.gov/pmc/articles/11192541","pdf_url":"https://pmc.ncbi.nlm.nih.gov/articles/PMC11192541/pdf/nihms-2000308.pdf","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":"ACS Catal","raw_type":"Text"},{"id":"pmh:oai:europepmc.org:10853724","doi":null,"is_oa":true,"landing_page_url":"https://www.ncbi.nlm.nih.gov/pmc/articles/11192541","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"}],"best_oa_location":{"id":"pmh:oai:pubmedcentral.nih.gov:11192541","doi":null,"is_oa":true,"landing_page_url":"https://www.ncbi.nlm.nih.gov/pmc/articles/11192541","pdf_url":"https://pmc.ncbi.nlm.nih.gov/articles/PMC11192541/pdf/nihms-2000308.pdf","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":"ACS Catal","raw_type":"Text"},"sustainable_development_goals":[],"study_designs":[],"awards":[{"id":"https://openalex.org/G1768011231","display_name":"Improving Small Molecule Synthesis by Controlling Reactions between Transition Metals and Carbon-Heteroatom Electrophiles","funder_award_id":"R35GM137971","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":{"pdf":true,"grobid_xml":true},"content_urls":{"pdf":"https://content.openalex.org/works/W4394728071.pdf","grobid_xml":"https://content.openalex.org/works/W4394728071.grobid-xml"},"referenced_works_count":51,"referenced_works":["https://openalex.org/W95426343","https://openalex.org/W1183155069","https://openalex.org/W1834860384","https://openalex.org/W1977469092","https://openalex.org/W1981876211","https://openalex.org/W1997374419","https://openalex.org/W2023864366","https://openalex.org/W2024617448","https://openalex.org/W2033255996","https://openalex.org/W2046016829","https://openalex.org/W2048311919","https://openalex.org/W2067312421","https://openalex.org/W2073213584","https://openalex.org/W2075266581","https://openalex.org/W2077307846","https://openalex.org/W2091702998","https://openalex.org/W2102784912","https://openalex.org/W2138537840","https://openalex.org/W2162106505","https://openalex.org/W2203318075","https://openalex.org/W2239806434","https://openalex.org/W2468336890","https://openalex.org/W2510551908","https://openalex.org/W2564831789","https://openalex.org/W2587427645","https://openalex.org/W2591703516","https://openalex.org/W2591867326","https://openalex.org/W2743592354","https://openalex.org/W2797849495","https://openalex.org/W2807831711","https://openalex.org/W2810262960","https://openalex.org/W2913425717","https://openalex.org/W2917126206","https://openalex.org/W2918150103","https://openalex.org/W2936743839","https://openalex.org/W2950216681","https://openalex.org/W2951964016","https://openalex.org/W2972122875","https://openalex.org/W3006337870","https://openalex.org/W3018981338","https://openalex.org/W3020719222","https://openalex.org/W3173320038","https://openalex.org/W3206212437","https://openalex.org/W3217390067","https://openalex.org/W4200462417","https://openalex.org/W4226128774","https://openalex.org/W4280587632","https://openalex.org/W4281392443","https://openalex.org/W4284970602","https://openalex.org/W4296381440","https://openalex.org/W4306407942"],"related_works":["https://openalex.org/W2497166291","https://openalex.org/W3051789148","https://openalex.org/W2552711547","https://openalex.org/W2605509999","https://openalex.org/W2045922702","https://openalex.org/W2123344285","https://openalex.org/W7165518240","https://openalex.org/W2056447453","https://openalex.org/W2110276191","https://openalex.org/W2949249168"],"abstract_inverted_index":{"This":[0],"report":[1],"describes":[2],"a":[3,45,98,138,166,169,238,264],"detailed":[4],"study":[5],"of":[6,14,29,40,71,83,101,155,165,174,227,232,240,263,267],"Ni":[7,170],"phosphine":[8,23,88],"catalysts":[9],"for":[10,61,94],"the":[11,41,72,81,134,163,175,196,224,248],"Suzuki\u2013Miyaura":[12],"coupling":[13],"dichloropyridines":[15,241],"with":[16,205,219,237],"halogen-containing":[17],"(hetero)aryl":[18],"boronic":[19,42,73,245],"acids.":[20,246],"With":[21,178],"most":[22],"ligands,":[24,183,211],"these":[25,84,156],"transformations":[26],"afford":[27,56,91,113],"mixtures":[28],"mono-":[30],"and":[31,53,59,107,121,132,147,209,242,254],"diarylated":[32,115],"cross-coupling":[33],"products":[34],"as":[35,37,65,67],"well":[36,66],"competing":[38,69],"oligomerization":[39,70],"acid.":[43,74],"However,":[44],"ligand":[46,193,213,250],"screen":[47],"revealed":[48],"that":[49,90,153],"PPh":[50,54],"2":[51,252],"Me":[52],"3":[55],"high":[57,92,143],"yield":[58],"selectivity":[60,82,93],"monoarylation":[62,95,144,262],"over":[63],"diarylation":[64,126],"minimal":[68],"Several":[75],"key":[76,167],"observations":[77],"were":[78],"made":[79],"regarding":[80],"reactions,":[85],"including:":[86],"(1)":[87],"ligands":[89],"fall":[96],"within":[97],"narrow":[99],"range":[100],"Tolman":[102],"cone":[103],"angles":[104],"(between":[105],"136":[106],"157\u00b0);":[108],"(2)":[109],"more":[110,180],"electron-rich":[111,119,181],"trialkylphosphines":[112],"predominantly":[114],"products,":[116],"while":[117],"less":[118],"di-":[120,208],"triarylphosphines":[122],"favor":[123],"monoarylation;":[124],"(3)":[125],"proceeds":[127],"via":[128],"intramolecular":[129,188],"oxidative":[130,189,220],"addition;":[131],"(4)":[133],"solvent":[135,255],"(MeCN)":[136,256],"plays":[137],"crucial":[139],"role":[140],"in":[141,223],"achieving":[142],"selectivity.":[145],"Experimental":[146],"density":[148],"functional":[149],"theory":[150],"studies":[151],"suggest":[152],"all":[154],"data":[157],"can":[158],"be":[159],"explained":[160],"based":[161],"on":[162],"reactivity":[164],"intermediate:":[168],"0":[171],"\u2013\u03c0":[172],"complex":[173,186],"monoarylated":[176,228],"product.":[177],"larger,":[179],"trialkylphosphine":[182],"this":[184,233],"\u03c0":[185],"undergoes":[187],"addition":[190],"faster":[191],"than":[192],"substitution":[194,214],"by":[195,215],"MeCN":[197,216],"solvent,":[198],"leading":[199],"to":[200,259],"selective":[201,225],"diarylation.":[202],"In":[203],"contrast,":[204],"relatively":[206],"small":[207],"triarylphosphine":[210],"associative":[212],"is":[217,235],"competitive":[218],"addition,":[221],"resulting":[222],"formation":[226],"products.":[229],"The":[230],"generality":[231],"method":[234],"demonstrated":[236],"variety":[239],"chloro-substituted":[243],"aryl":[244],"Furthermore,":[247],"optimal":[249],"(PPh":[251],"Me)":[253],"are":[257],"leveraged":[258],"achieve":[260],"Ni-catalyzed":[261],"broader":[265],"set":[266],"dichloroarene":[268],"substrates.":[269]},"counts_by_year":[{"year":2026,"cited_by_count":2},{"year":2025,"cited_by_count":5},{"year":2024,"cited_by_count":2}],"updated_date":"2026-10-29T09:56:32.521200","created_date":"2024-04-12T00:00:00"}
