{"id":"https://openalex.org/W4306822733","doi":"https://doi.org/10.1021/acscatal.2c04490","title":"Key Selectivity Controlling Elements in Rhodium-Catalyzed C\u2013H Functionalization with Donor/Acceptor Carbenes","display_name":"Key Selectivity Controlling Elements in Rhodium-Catalyzed C\u2013H Functionalization with Donor/Acceptor Carbenes","publication_year":2022,"publication_date":"2022-10-19","ids":{"openalex":"https://openalex.org/W4306822733","doi":"https://doi.org/10.1021/acscatal.2c04490"},"language":"en","primary_location":{"id":"doi:10.1021/acscatal.2c04490","doi":"https://doi.org/10.1021/acscatal.2c04490","is_oa":false,"landing_page_url":"https://doi.org/10.1021/acscatal.2c04490","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","indexed_in":["crossref"],"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/A5056603372","display_name":"Zhi Min Ren","orcid":"https://orcid.org/0000-0001-9812-0251","observed_orcids":["https://orcid.org/0000-0001-9812-0251"]},"institutions":[{"id":"https://openalex.org/I150468666","display_name":"Emory University","ror":"https://ror.org/03czfpz43","country_code":"US","type":"education","lineage":["https://openalex.org/I150468666"]},{"id":"https://openalex.org/I4210152380","display_name":"Shenzhen Technology University","ror":"https://ror.org/04qzpec27","country_code":"CN","type":"education","lineage":["https://openalex.org/I4210152380"]}],"countries":["CN","US"],"is_corresponding":true,"raw_author_name":"Zhi Ren","raw_affiliation_strings":["College of Pharmacy, Shenzhen Technology University, 3002 Lantian Road, Shenzhen, Guangdong, China 518118","Department of Chemistry, Emory University, 1515 Dickey Drive, Atlanta, Georgia 30322, United States"],"raw_orcid":"https://orcid.org/0000-0001-9812-0251","affiliations":[{"raw_affiliation_string":"College of Pharmacy, Shenzhen Technology University, 3002 Lantian Road, Shenzhen, Guangdong, China 518118","institution_ids":["https://openalex.org/I4210152380"]},{"raw_affiliation_string":"Department of Chemistry, Emory University, 1515 Dickey Drive, Atlanta, Georgia 30322, United States","institution_ids":["https://openalex.org/I150468666"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5012743614","display_name":"Djamaladdin G. Musaev","orcid":"https://orcid.org/0000-0003-1160-6131","observed_orcids":["https://orcid.org/0000-0003-1160-6131"]},"institutions":[{"id":"https://openalex.org/I150468666","display_name":"Emory University","ror":"https://ror.org/03czfpz43","country_code":"US","type":"education","lineage":["https://openalex.org/I150468666"]}],"countries":["US"],"is_corresponding":true,"raw_author_name":"Djamaladdin G. Musaev","raw_affiliation_strings":["Cherry L. Emerson Center for Scientific Computation, Emory University, 1521 Dickey Drive, Atlanta, Georgia 30322, United States","Department of Chemistry, Emory University, 1515 Dickey Drive, Atlanta, Georgia 30322, United States"],"raw_orcid":"https://orcid.org/0000-0003-1160-6131","affiliations":[{"raw_affiliation_string":"Cherry L. Emerson Center for Scientific Computation, Emory University, 1521 Dickey Drive, Atlanta, Georgia 30322, United States","institution_ids":["https://openalex.org/I150468666"]},{"raw_affiliation_string":"Department of Chemistry, Emory University, 1515 Dickey Drive, Atlanta, Georgia 30322, United States","institution_ids":["https://openalex.org/I150468666"]}]},{"author_position":"last","author":{"id":"https://openalex.org/A5083948798","display_name":"Huw M. L. Davies","orcid":"https://orcid.org/0000-0001-6254-9398","observed_orcids":["https://orcid.org/0000-0001-6254-9398"]},"institutions":[{"id":"https://openalex.org/I150468666","display_name":"Emory University","ror":"https://ror.org/03czfpz43","country_code":"US","type":"education","lineage":["https://openalex.org/I150468666"]}],"countries":["US"],"is_corresponding":true,"raw_author_name":"Huw M. L. Davies","raw_affiliation_strings":["Department of Chemistry, Emory University, 1515 Dickey Drive, Atlanta, Georgia 30322, United States"],"raw_orcid":"https://orcid.org/0000-0001-6254-9398","affiliations":[{"raw_affiliation_string":"Department of Chemistry, Emory University, 1515 Dickey Drive, Atlanta, Georgia 30322, United States","institution_ids":["https://openalex.org/I150468666"]}]}],"institutions":[],"countries_distinct_count":2,"institutions_distinct_count":2,"corresponding_author_ids":["https://openalex.org/A5012743614","https://openalex.org/A5056603372","https://openalex.org/A5083948798"],"corresponding_institution_ids":["https://openalex.org/I150468666","https://openalex.org/I4210152380"],"apc_list":{"value":5000,"currency":"USD","value_usd":5000},"apc_paid":null,"fwci":1.5947,"has_fulltext":false,"cited_by_count":23,"citation_normalized_percentile":{"value":0.82017224,"is_in_top_1_percent":false,"is_in_top_10_percent":false},"cited_by_percentile_year":{"min":96,"max":99},"biblio":{"volume":"12","issue":"21","first_page":"13446","last_page":"13456"},"is_retracted":false,"is_paratext":false,"is_xpac":false,"primary_topic":{"id":"https://openalex.org/T11611","display_name":"Cyclopropane Reaction Mechanisms","score":0.9945999979972839,"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/T11611","display_name":"Cyclopropane Reaction Mechanisms","score":0.9945999979972839,"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/T11790","display_name":"N-Heterocyclic Carbenes in Organic and Inorganic Chemistry","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/T10354","display_name":"Catalytic C\u2013H Functionalization Methods","score":0.0010999999940395355,"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/rhodium-catalysis","display_name":"rhodium catalysis","score":0.9440000057220459},{"id":"https://openalex.org/keywords/c-h-functionalization","display_name":"C\u2013H functionalization","score":0.968999981880188},{"id":"https://openalex.org/keywords/enantioselectivity","display_name":"enantioselectivity","score":0.9070000052452087},{"id":"https://openalex.org/keywords/site-selectivity","display_name":"site selectivity","score":0.843999981880188},{"id":"https://openalex.org/keywords/nitrogen-extrusion","display_name":"nitrogen extrusion","score":0.9359999895095825},{"id":"https://openalex.org/keywords/carbene-insertion","display_name":"carbene insertion","score":0.8399999737739563},{"id":"https://openalex.org/keywords/curtin-hammett-principle","display_name":"Curtin-Hammett principle","score":0.7829999923706055},{"id":"https://openalex.org/keywords/diastereomeric-ratio","display_name":"diastereomeric ratio","score":0.6169999837875366}],"concepts":[{"id":"https://openalex.org/C2777164566","wikidata":"https://www.wikidata.org/wiki/Q419257","display_name":"Carbene","level":3,"score":0.9463632106781006},{"id":"https://openalex.org/C185592680","wikidata":"https://www.wikidata.org/wiki/Q2329","display_name":"Chemistry","level":0,"score":0.8396563529968262},{"id":"https://openalex.org/C138716334","wikidata":"https://www.wikidata.org/wiki/Q268477","display_name":"Diastereomer","level":2,"score":0.8272261619567871},{"id":"https://openalex.org/C521398313","wikidata":"https://www.wikidata.org/wiki/Q1087","display_name":"Rhodium","level":3,"score":0.8082792162895203},{"id":"https://openalex.org/C18705241","wikidata":"https://www.wikidata.org/wiki/Q1128023","display_name":"Conformational isomerism","level":3,"score":0.6240677833557129},{"id":"https://openalex.org/C161790260","wikidata":"https://www.wikidata.org/wiki/Q82264","display_name":"Catalysis","level":2,"score":0.5459732413291931},{"id":"https://openalex.org/C2776904781","wikidata":"https://www.wikidata.org/wiki/Q424424","display_name":"Diazo","level":2,"score":0.48896634578704834},{"id":"https://openalex.org/C146686406","wikidata":"https://www.wikidata.org/wiki/Q898628","display_name":"Enantioselective synthesis","level":3,"score":0.4433605670928955},{"id":"https://openalex.org/C86914705","wikidata":"https://www.wikidata.org/wiki/Q414293","display_name":"Transition metal carbene complex","level":4,"score":0.41130921244621277},{"id":"https://openalex.org/C71240020","wikidata":"https://www.wikidata.org/wiki/Q186011","display_name":"Stereochemistry","level":1,"score":0.38951072096824646},{"id":"https://openalex.org/C155647269","wikidata":"https://www.wikidata.org/wiki/Q243455","display_name":"Medicinal chemistry","level":1,"score":0.36498159170150757},{"id":"https://openalex.org/C75473681","wikidata":"https://www.wikidata.org/wiki/Q188651","display_name":"Photochemistry","level":1,"score":0.3393564820289612},{"id":"https://openalex.org/C178790620","wikidata":"https://www.wikidata.org/wiki/Q11351","display_name":"Organic chemistry","level":1,"score":0.23057106137275696},{"id":"https://openalex.org/C32909587","wikidata":"https://www.wikidata.org/wiki/Q11369","display_name":"Molecule","level":2,"score":0.1774490773677826}],"mesh":[],"locations_count":1,"locations":[{"id":"doi:10.1021/acscatal.2c04490","doi":"https://doi.org/10.1021/acscatal.2c04490","is_oa":false,"landing_page_url":"https://doi.org/10.1021/acscatal.2c04490","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"}],"best_oa_location":null,"sustainable_development_goals":[],"study_designs":[],"awards":[{"id":"https://openalex.org/G803071204","display_name":"NSF Center for Selective CH Functionalization","funder_award_id":"1700982","funder_id":"https://openalex.org/F4320306076","funder_display_name":"National Science Foundation"}],"funders":[{"id":"https://openalex.org/F4320306076","display_name":"National Science Foundation","ror":"https://ror.org/021nxhr62"}],"has_content":{"grobid_xml":false,"pdf":false},"content_urls":null,"referenced_works_count":72,"referenced_works":["https://openalex.org/W1804234511","https://openalex.org/W1878013350","https://openalex.org/W1926827464","https://openalex.org/W1966182479","https://openalex.org/W1969457598","https://openalex.org/W1980154609","https://openalex.org/W1982356449","https://openalex.org/W1984232099","https://openalex.org/W1987731015","https://openalex.org/W1989156004","https://openalex.org/W2007330836","https://openalex.org/W2008844584","https://openalex.org/W2009904876","https://openalex.org/W2013665598","https://openalex.org/W2019954899","https://openalex.org/W2023271753","https://openalex.org/W2028117546","https://openalex.org/W2033817758","https://openalex.org/W2035228670","https://openalex.org/W2037201782","https://openalex.org/W2039559098","https://openalex.org/W2040041008","https://openalex.org/W2042796027","https://openalex.org/W2044490585","https://openalex.org/W2058848030","https://openalex.org/W2067011309","https://openalex.org/W2068418204","https://openalex.org/W2068617439","https://openalex.org/W2080709819","https://openalex.org/W2086957099","https://openalex.org/W2088943937","https://openalex.org/W2092157292","https://openalex.org/W2111728712","https://openalex.org/W2140153358","https://openalex.org/W2160849633","https://openalex.org/W2170261800","https://openalex.org/W2186842654","https://openalex.org/W2190446545","https://openalex.org/W2264038220","https://openalex.org/W2273094461","https://openalex.org/W2283724313","https://openalex.org/W2312778188","https://openalex.org/W2314599242","https://openalex.org/W2317020669","https://openalex.org/W2318135678","https://openalex.org/W2324407439","https://openalex.org/W2327812706","https://openalex.org/W2333507101","https://openalex.org/W2340195186","https://openalex.org/W2346072123","https://openalex.org/W2379591351","https://openalex.org/W2404140389","https://openalex.org/W2475633076","https://openalex.org/W2489957181","https://openalex.org/W2495633209","https://openalex.org/W2600397526","https://openalex.org/W2601190908","https://openalex.org/W2769205387","https://openalex.org/W2884278463","https://openalex.org/W2892082086","https://openalex.org/W2897571102","https://openalex.org/W2899053766","https://openalex.org/W2900482408","https://openalex.org/W2905531315","https://openalex.org/W2931660567","https://openalex.org/W2944003111","https://openalex.org/W2944679719","https://openalex.org/W2966664658","https://openalex.org/W2969819767","https://openalex.org/W2986107128","https://openalex.org/W3015820775","https://openalex.org/W3080403564"],"related_works":["https://openalex.org/W3015820775","https://openalex.org/W2013665598","https://openalex.org/W7118781132","https://openalex.org/W2312778188","https://openalex.org/W4408907876","https://openalex.org/W2889806851","https://openalex.org/W1988547968","https://openalex.org/W2314599242","https://openalex.org/W4392763805","https://openalex.org/W4389547358"],"abstract_inverted_index":{"Computational":[0],"studies":[1],"on":[2,152,191],"the":[3,12,22,28,32,41,50,62,68,86,89,98,107,115,132,139,142,146,149,153,168,175,182,192,197,200,204,215,224,234,247],"dirhodium(tetracarboxylate)-catalyzed":[4],"C\u2013H":[5,52,179],"functionalization":[6],"with":[7,203,255],"donor/acceptor":[8],"carbenes":[9],"reveal":[10],"that":[11,97],"enantioselectivity":[13,195,245],"and":[14,31,36,46,70,72,145,194],"site-selectivity":[15],"of":[16,24,26,40,119,134,141,148,196,246,259],"this":[17],"reaction":[18,99],"are":[19],"controlled":[20],"by":[21,138],"ratio":[23,133,140],"conformers":[25,144],"both":[27],"diazo":[29],"compound":[30],"dirhodium":[33,75,124],"carbene":[34,47,63,125,159,186,218,237],"intermediates":[35,126],"two":[37,93,183],"distinct":[38],"steps":[39],"reaction,":[42,214,248],"namely,":[43],"nitrogen":[44,110,154],"extrusion":[45,111],"insertion":[48],"in":[49,92,162,228,252],"functionalized":[51],"bond.":[53],"In":[54,199],"these":[55],"studies,":[56],"we":[57,95],"used":[58],"trichloroethyl":[59],"phenyldiazoacetate":[60],"as":[61,67,85,128],"precursor,":[64],"p":[65,82,210],"-isopropyltoluene":[66],"substrate,":[69],"dirhodium-tetraacetate":[71],"a":[73,129,229],"chiral":[74,150],"complex,":[76],"Rh":[77,205],"2":[78,206],"(":[79,207],"S":[80,208],"-":[81,209],"-BrTPCP)":[83,211],"4,":[84],"catalysts.":[87],"While":[88],"aryldiazoacetate":[90,120,143],"exists":[91],"conformers,":[94],"found":[96],"is":[100,112,136,172,220,251],"not":[101],"under":[102],"Curtin":[103],"Hammett":[104],"conditions":[105],"because":[106],"barrier":[108,116,169,176],"for":[109,117,170,177],"less":[113],"than":[114,174],"interconversion":[118],"conformers.":[121],"The":[122,156,242],"resulting":[123],"exist":[127],"diastereomeric":[130,157,184],"mixture,":[131],"which":[135],"governed":[137],"influence":[147],"catalyst":[151],"extrusion.":[155],"rhodium":[158,185,217,236],"complexes":[160,187],"can,":[161],"principle,":[163],"interconvert":[164],"through":[165],"rotation,":[166],"but":[167],"rotation":[171],"greater":[173],"benzylic":[178],"functionalization.":[180],"Thus,":[181],"have":[188],"different":[189],"influences":[190],"site-":[193],"reaction.":[198],"particular":[201],"case":[202],"4":[212],"-catalyzed":[213],"major":[216],"diastereomer":[219,238],"calculated":[221],"to":[222],"be":[223],"matched":[225],"case,":[226],"reacting":[227],"highly":[230],"enantioselective":[231],"manner,":[232],"whereas":[233],"minor":[235],"gives":[239],"low":[240],"enantioselectivity.":[241],"overall":[243],"predicted":[244],"98.9:1.1":[249],"er,":[250],"close":[253],"agreement":[254],"its":[256],"observed":[257],"value":[258],"97.5:2.5":[260],"er.":[261]},"counts_by_year":[{"year":2026,"cited_by_count":6},{"year":2025,"cited_by_count":8},{"year":2024,"cited_by_count":5},{"year":2023,"cited_by_count":4}],"updated_date":"2026-11-05T12:25:35.769452","created_date":"2022-10-20T00:00:00"}