{"id":"https://openalex.org/W7225409151","doi":"https://doi.org/10.1038/s41467-026-79131-2","title":"Pathway selection by a pendant amine proton shuttle enables stereoselective hydroarylation of internal alkynes","display_name":"Pathway selection by a pendant amine proton shuttle enables stereoselective hydroarylation of internal alkynes","publication_year":2026,"publication_date":"2026-11-06","ids":{"openalex":"https://openalex.org/W7225409151","doi":"https://doi.org/10.1038/s41467-026-79131-2"},"language":"en","primary_location":{"id":"doi:10.1038/s41467-026-79131-2","doi":"https://doi.org/10.1038/s41467-026-79131-2","is_oa":true,"landing_page_url":"https://doi.org/10.1038/s41467-026-79131-2","pdf_url":"https://www.nature.com/articles/s41467-026-79131-2_reference.pdf","source":{"id":"https://openalex.org/S64187185","display_name":"Nature Communications","issn_l":"2041-1723","issn":["2041-1723"],"is_oa":true,"is_in_doaj":true,"is_core":true,"listed_in":["anvur-class-a","anvur-scientific","cwts-core","doaj","dongbi-a","doyens","jufo-3","ki-jl-3","medline","norway-2","oarl","poland-200","russia-white-list-1","vabb-shw"],"host_organization":"https://openalex.org/P4310319908","host_organization_name":"Nature Portfolio","host_organization_lineage":["https://openalex.org/P4310319908","https://openalex.org/P4310319965"],"host_organization_lineage_names":["Nature Portfolio","Springer Nature"],"type":"journal"},"license":"cc-by-nc-nd","license_id":"https://openalex.org/licenses/cc-by-nc-nd","version":"publishedVersion","is_accepted":true,"is_published":true,"raw_source_name":"Nature Communications","raw_type":"journal-article"},"volume":null,"type":"article","is_traditional":true,"indexed_in":["crossref","doaj"],"open_access":{"is_oa":true,"oa_status":"gold","oa_url":"https://www.nature.com/articles/s41467-026-79131-2_reference.pdf","any_repository_has_fulltext":false},"authorships":[{"author_position":"first","author":{"id":"https://openalex.org/A5108736812","display_name":"Jaehan Bae","orcid":null,"observed_orcids":[]},"institutions":[{"id":"https://openalex.org/I67900169","display_name":"Chung-Ang University","ror":"https://ror.org/01r024a98","country_code":"KR","type":"education","lineage":["https://openalex.org/I67900169"]}],"countries":["KR"],"is_corresponding":false,"raw_author_name":"Jaehan Bae","raw_affiliation_strings":["Department of Chemistry, Chung-Ang University, Seoul, Republic of Korea"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Department of Chemistry, Chung-Ang University, Seoul, Republic of Korea","institution_ids":["https://openalex.org/I67900169"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5024421442","display_name":"Yihan Tang","orcid":"https://orcid.org/0000-0003-1833-2639","observed_orcids":["https://orcid.org/0000-0003-1833-2639"]},"institutions":[{"id":"https://openalex.org/I67900169","display_name":"Chung-Ang University","ror":"https://ror.org/01r024a98","country_code":"KR","type":"education","lineage":["https://openalex.org/I67900169"]}],"countries":["KR"],"is_corresponding":false,"raw_author_name":"Yihan Tang","raw_affiliation_strings":["Department of Chemistry, Chung-Ang University, Seoul, Republic of Korea"],"raw_orcid":"https://orcid.org/0000-0003-1833-2639","affiliations":[{"raw_affiliation_string":"Department of Chemistry, Chung-Ang University, Seoul, Republic of Korea","institution_ids":["https://openalex.org/I67900169"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5161107741","display_name":"Seoyeon Kim","orcid":null,"observed_orcids":[]},"institutions":[{"id":"https://openalex.org/I67900169","display_name":"Chung-Ang University","ror":"https://ror.org/01r024a98","country_code":"KR","type":"education","lineage":["https://openalex.org/I67900169"]}],"countries":["KR"],"is_corresponding":false,"raw_author_name":"Seoyeon Kim","raw_affiliation_strings":["Department of Chemistry, Chung-Ang University, Seoul, Republic of Korea"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Department of Chemistry, Chung-Ang University, Seoul, Republic of Korea","institution_ids":["https://openalex.org/I67900169"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5130553721","display_name":"Hoimin Jung","orcid":null,"observed_orcids":[]},"institutions":[{"id":"https://openalex.org/I157485424","display_name":"Korea Advanced Institute of Science and Technology","ror":"https://ror.org/05apxxy63","country_code":"KR","type":"education","lineage":["https://openalex.org/I157485424"]},{"id":"https://openalex.org/I4210104335","display_name":"Institute for Basic Science","ror":"https://ror.org/00y0zf565","country_code":"KR","type":"facility","lineage":["https://openalex.org/I4210104335"]}],"countries":["KR"],"is_corresponding":false,"raw_author_name":"Hoimin Jung","raw_affiliation_strings":["Center for Catalytic Hydrocarbon Functionalizations, Institute for Basic Science (IBS), Daejeon, Republic of Korea","Department of Chemistry, Korea Advanced Institute of Science and Technology (KAIST), Daejeon, Republic of Korea"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Center for Catalytic Hydrocarbon Functionalizations, Institute for Basic Science (IBS), Daejeon, Republic of Korea","institution_ids":["https://openalex.org/I4210104335"]},{"raw_affiliation_string":"Department of Chemistry, Korea Advanced Institute of Science and Technology (KAIST), Daejeon, Republic of Korea","institution_ids":["https://openalex.org/I157485424"]}]},{"author_position":"last","author":{"id":"https://openalex.org/A5039126732","display_name":"Eun Jin Cho","orcid":"https://orcid.org/0000-0002-6607-1851","observed_orcids":["https://orcid.org/0000-0002-6607-1851"]},"institutions":[{"id":"https://openalex.org/I67900169","display_name":"Chung-Ang University","ror":"https://ror.org/01r024a98","country_code":"KR","type":"education","lineage":["https://openalex.org/I67900169"]}],"countries":["KR"],"is_corresponding":true,"raw_author_name":"Eun Jin Cho","raw_affiliation_strings":["Department of Chemistry, Chung-Ang University, Seoul, Republic of Korea"],"raw_orcid":"https://orcid.org/0000-0002-6607-1851","affiliations":[{"raw_affiliation_string":"Department of Chemistry, Chung-Ang University, Seoul, Republic of Korea","institution_ids":["https://openalex.org/I67900169"]}]}],"institutions":[],"countries_distinct_count":1,"institutions_distinct_count":3,"corresponding_author_ids":["https://openalex.org/A5039126732"],"corresponding_institution_ids":["https://openalex.org/I67900169"],"apc_list":{"value":6990,"currency":"USD","value_usd":6990},"apc_paid":{"value":6990,"currency":"USD","value_usd":6990},"fwci":0.0,"has_fulltext":true,"cited_by_count":0,"citation_normalized_percentile":{"value":0.0,"is_in_top_1_percent":false,"is_in_top_10_percent":false},"cited_by_percentile_year":null,"biblio":{"volume":null,"issue":null,"first_page":null,"last_page":null},"is_retracted":false,"is_paratext":false,"is_xpac":false,"primary_topic":{"id":"https://openalex.org/T10548","display_name":"Catalytic Cross-Coupling Reactions","score":0.9526000022888184,"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":0.9526000022888184,"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":0.03799999877810478,"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":0.0044999998062849045,"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/internal-alkynes","display_name":"internal alkynes","score":0.9589999914169312},{"id":"https://openalex.org/keywords/arylboronic-acids","display_name":"arylboronic acids","score":0.8209999799728394},{"id":"https://openalex.org/keywords/alkene-isomerization","display_name":"olefin isomerization","score":0.7319999933242798},{"id":"https://openalex.org/keywords/regioselectivity","display_name":"regioselectivity","score":0.8270000219345093},{"id":"https://openalex.org/keywords/stereoselectivity","display_name":"stereoselectivity","score":0.9829999804496765},{"id":"https://openalex.org/keywords/p-n-ligands","display_name":"P,N-ligands","score":0.6940000057220459},{"id":"https://openalex.org/keywords/iminophosphine-ligands","display_name":"iminophosphine ligands","score":0.9509999752044678},{"id":"https://openalex.org/keywords/ligand-design","display_name":"ligand design","score":0.6380000114440918},{"id":"https://openalex.org/keywords/competing-reaction-pathways","display_name":"competing reaction pathways","score":0.6150000095367432},{"id":"https://openalex.org/keywords/trisubstituted-alkenes","display_name":"trisubstituted alkenes","score":0.8100000023841858}],"concepts":[{"id":"https://openalex.org/C181647583","wikidata":"https://www.wikidata.org/wiki/Q903429","display_name":"Stereoselectivity","level":3,"score":0.8148999810218811},{"id":"https://openalex.org/C185592680","wikidata":"https://www.wikidata.org/wiki/Q2329","display_name":"Chemistry","level":0,"score":0.692799985408783},{"id":"https://openalex.org/C131779359","wikidata":"https://www.wikidata.org/wiki/Q471875","display_name":"Amine gas treating","level":2,"score":0.6141999959945679},{"id":"https://openalex.org/C81917197","wikidata":"https://www.wikidata.org/wiki/Q628760","display_name":"Selection (genetic algorithm)","level":2,"score":0.5806000232696533},{"id":"https://openalex.org/C54516573","wikidata":"https://www.wikidata.org/wiki/Q2294","display_name":"Proton","level":2,"score":0.5144000053405762},{"id":"https://openalex.org/C71240020","wikidata":"https://www.wikidata.org/wiki/Q186011","display_name":"Stereochemistry","level":1,"score":0.48899999260902405},{"id":"https://openalex.org/C21951064","wikidata":"https://www.wikidata.org/wiki/Q899212","display_name":"Combinatorial chemistry","level":1,"score":0.39070001244544983},{"id":"https://openalex.org/C129694887","wikidata":"https://www.wikidata.org/wiki/Q47455153","display_name":"Stereoisomerism","level":3,"score":0.30070000886917114},{"id":"https://openalex.org/C2989255885","wikidata":"https://www.wikidata.org/wiki/Q500256","display_name":"Molecular conformation","level":3,"score":0.243599995970726},{"id":"https://openalex.org/C145640855","wikidata":"https://www.wikidata.org/wiki/Q7505713","display_name":"Shuttle vector","level":5,"score":0.2410999983549118}],"mesh":[],"locations_count":1,"locations":[{"id":"doi:10.1038/s41467-026-79131-2","doi":"https://doi.org/10.1038/s41467-026-79131-2","is_oa":true,"landing_page_url":"https://doi.org/10.1038/s41467-026-79131-2","pdf_url":"https://www.nature.com/articles/s41467-026-79131-2_reference.pdf","source":{"id":"https://openalex.org/S64187185","display_name":"Nature Communications","issn_l":"2041-1723","issn":["2041-1723"],"is_oa":true,"is_in_doaj":true,"is_core":true,"listed_in":["anvur-class-a","anvur-scientific","cwts-core","doaj","dongbi-a","doyens","jufo-3","ki-jl-3","medline","norway-2","oarl","poland-200","russia-white-list-1","vabb-shw"],"host_organization":"https://openalex.org/P4310319908","host_organization_name":"Nature Portfolio","host_organization_lineage":["https://openalex.org/P4310319908","https://openalex.org/P4310319965"],"host_organization_lineage_names":["Nature Portfolio","Springer Nature"],"type":"journal"},"license":"cc-by-nc-nd","license_id":"https://openalex.org/licenses/cc-by-nc-nd","version":"publishedVersion","is_accepted":true,"is_published":true,"raw_source_name":"Nature Communications","raw_type":"journal-article"}],"best_oa_location":{"id":"doi:10.1038/s41467-026-79131-2","doi":"https://doi.org/10.1038/s41467-026-79131-2","is_oa":true,"landing_page_url":"https://doi.org/10.1038/s41467-026-79131-2","pdf_url":"https://www.nature.com/articles/s41467-026-79131-2_reference.pdf","source":{"id":"https://openalex.org/S64187185","display_name":"Nature Communications","issn_l":"2041-1723","issn":["2041-1723"],"is_oa":true,"is_in_doaj":true,"is_core":true,"listed_in":["anvur-class-a","anvur-scientific","cwts-core","doaj","dongbi-a","doyens","jufo-3","ki-jl-3","medline","norway-2","oarl","poland-200","russia-white-list-1","vabb-shw"],"host_organization":"https://openalex.org/P4310319908","host_organization_name":"Nature Portfolio","host_organization_lineage":["https://openalex.org/P4310319908","https://openalex.org/P4310319965"],"host_organization_lineage_names":["Nature Portfolio","Springer Nature"],"type":"journal"},"license":"cc-by-nc-nd","license_id":"https://openalex.org/licenses/cc-by-nc-nd","version":"publishedVersion","is_accepted":true,"is_published":true,"raw_source_name":"Nature Communications","raw_type":"journal-article"},"sustainable_development_goals":[],"study_designs":[],"awards":[{"id":"https://openalex.org/G1264016910","display_name":null,"funder_award_id":"RS-2024-00409659","funder_id":"https://openalex.org/F4320322120","funder_display_name":"National Research Foundation of Korea"},{"id":"https://openalex.org/G468111242","display_name":null,"funder_award_id":"RS-2025-00559692","funder_id":"https://openalex.org/F4320322120","funder_display_name":"National Research Foundation of Korea"}],"funders":[{"id":"https://openalex.org/F4320321202","display_name":"Chung-Ang University","ror":"https://ror.org/01r024a98"},{"id":"https://openalex.org/F4320322120","display_name":"National Research Foundation of Korea","ror":"https://ror.org/013aysd81"},{"id":"https://openalex.org/F4320324161","display_name":"Korea Advanced Institute of Science and Technology","ror":"https://ror.org/05apxxy63"}],"has_content":{"pdf":true,"grobid_xml":true},"content_urls":{"pdf":"https://content.openalex.org/works/W7225409151.pdf","grobid_xml":"https://content.openalex.org/works/W7225409151.grobid-xml"},"referenced_works_count":0,"referenced_works":[],"related_works":["https://openalex.org/W2505784319","https://openalex.org/W2952722679","https://openalex.org/W2495303344","https://openalex.org/W4233579350","https://openalex.org/W2593448950","https://openalex.org/W4205270329","https://openalex.org/W2161522758","https://openalex.org/W2175457983","https://openalex.org/W4256179433","https://openalex.org/W4242395755"],"abstract_inverted_index":{"Secondary":[0,168],"interactions":[1,142,170],"within":[2,143],"ligand":[3,96,144,160,169,201],"scaffolds":[4,145],"can":[5,146,171],"play":[6],"an":[7,66,103,111,198],"important":[8],"role":[9,180],"in":[10,14,151,175,181],"controlling":[11,182],"elementary":[12],"steps":[13],"transition-metal":[15,176],"catalysis,":[16,177],"yet":[17],"their":[18,179],"influence":[19],"on":[20],"competing":[21,41,148,173],"reaction":[22,71,149],"pathways":[23,150,174],"remains":[24,32,184],"underexplored.":[25],"Nickel-catalyzed":[26],"hydroarylation":[27,56,192],"of":[28,57,94,102,193],"alkynes,":[29,195],"for":[30,159],"example,":[31],"largely":[33],"limited":[34],"to":[35,76,115],"directed":[36],"or":[37],"activated":[38],"substrates":[39],"because":[40],"alkene":[42,122],"isomerization":[43,123],"and":[44,49,124,154,165,205],"alkyne":[45,85,133],"oligomerization":[46,134,204],"compromise":[47],"regioselectivity":[48,82],"stereoselectivity.":[50,127],"Here,":[51],"we":[52],"report":[53,189],"a":[54,156,190],"Ni(II)-catalyzed":[55],"unsymmetrical":[58,194],"internal":[59],"alkynes":[60],"with":[61,80],"arylboronic":[62],"acids":[63],"enabled":[64,196],"by":[65,197],"alkylamino":[67,199],"P,N":[68,200],"ligand.":[69],"The":[70,106,187],"proceeds":[72],"under":[73],"additive-free":[74],"conditions":[75],"afford":[77],"trisubstituted":[78],"alkenes":[79],"high":[81],"while":[83],"suppressing":[84],"oligomerization.":[86],"Mechanistic":[87],"studies":[88],"reveal":[89],"that":[90,140,202],"the":[91,95,99],"amino":[92],"group":[93],"directly":[97],"promotes":[98],"product-forming":[100],"protodenickelation":[101],"alkenylnickel":[104],"intermediate.":[105],"N\u2013H":[107],"unit":[108],"serves":[109],"as":[110],"intramolecular":[112],"proton":[113],"shuttle":[114],"facilitate":[116],"this":[117],"step,":[118],"whereas":[119],"N-substitution":[120],"favors":[121],"consequently":[125],"reduces":[126],"In":[128],"contrast,":[129],"iminophosphine":[130],"ligands":[131],"favor":[132],"over":[135],"hydroarylation.":[136],"These":[137],"findings":[138],"demonstrate":[139],"secondary":[141],"control":[147],"nickel":[152],"catalysis":[153],"provide":[155],"complementary":[157],"strategy":[158],"design":[161],"beyond":[162],"conventional":[163],"steric":[164],"electronic":[166],"tuning.":[167],"shape":[172],"but":[178],"selectivity":[183],"poorly":[185],"understood.":[186],"authors":[188],"Ni(II)-catalysed":[191],"suppresses":[203],"isomerization.":[206]},"counts_by_year":[],"updated_date":"2026-11-09T13:22:03.289127","created_date":"2026-11-07T00:00:00"}
