Iridium-Catalyzed Enantioselective Alkene Hydroalkylation via a Heteroaryl-Directed Enolization–Decarboxylation Sequence
Upon exposure to a cationic Ir(I)-complex modified with the chiral diphosphine DuanPhos, hydroalkylations of styrenes and α-olefins with diverse heteroaryl tert-butyl acetates occur with complete branched selectivity and very high enantioselectivity. The initial adducts undergo acid promoted decarb...
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| Published in | Journal of the American Chemical Society Vol. 145; no. 44; pp. 23918 - 23924 |
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| Main Authors | , , |
| Format | Journal Article |
| Language | English |
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American Chemical Society
08.11.2023
Amer Chemical Soc |
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| Abstract | Upon exposure to a cationic Ir(I)-complex modified with the chiral diphosphine DuanPhos, hydroalkylations of styrenes and α-olefins with diverse heteroaryl tert-butyl acetates occur with complete branched selectivity and very high enantioselectivity. The initial adducts undergo acid promoted decarboxylation in situ to provide alkylated heteroarenes possessing defined β-stereocenters. The processes are postulated to proceed via a stereodefined chiral Ir-enolate, which arises upon heteroarene directed enolization of the heteroaryl acetate precursor. The method can be classified as an enantioselective decarboxylative C(sp3)–C(sp3) cross-coupling. |
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| AbstractList | Upon exposure to a cationic Ir(I)-complex modified with the chiral diphosphine DuanPhos, hydroalkylations of styrenes and α-olefins with diverse heteroaryl tert-butyl acetates occur with complete branched selectivity and very high enantioselectivity. The initial adducts undergo acid promoted decarboxylation in situ to provide alkylated heteroarenes possessing defined β-stereocenters. The processes are postulated to proceed via a stereodefined chiral Ir-enolate, which arises upon heteroarene directed enolization of the heteroaryl acetate precursor. The method can be classified as an enantioselective decarboxylative C(sp3)–C(sp3) cross-coupling. Upon exposure to a cationic Ir(I)-complex modified with the chiral diphosphine DuanPhos, hydroalkylations of styrenes and alpha-olefins with diverse heteroaryl tert-butyl acetates occur with complete branched selectivity and very high enantioselectivity. The initial adducts undergo acid promoted decarboxylation in situ to provide alkylated heteroarenes possessing defined beta-stereocenters. The processes are postulated to proceed via a stereodefined chiral Ir-enolate, which arises upon heteroarene directed enolization of the heteroaryl acetate precursor. The method can be classified as an enantioselective decarboxylative C(sp(3))-C(sp(3)) cross-coupling. Upon exposure to a cationic Ir(I)-complex modified with the chiral diphosphine DuanPhos, hydroalkylations of styrenes and α-olefins with diverse heteroaryl tert-butyl acetates occur with complete branched selectivity and very high enantioselectivity. The initial adducts undergo acid promoted decarboxylation in situ to provide alkylated heteroarenes possessing defined β-stereocenters. The processes are postulated to proceed via a stereodefined chiral Ir-enolate, which arises upon heteroarene directed enolization of the heteroaryl acetate precursor. The method can be classified as an enantioselective decarboxylative C(sp3)-C(sp3) cross-coupling. Upon exposure to a cationic Ir(I)-complex modified with the chiral diphosphine DuanPhos, hydroalkylations of styrenes and α-olefins with diverse heteroaryl tert -butyl acetates occur with complete branched selectivity and very high enantioselectivity. The initial adducts undergo acid promoted decarboxylation in situ to provide alkylated heteroarenes possessing defined β-stereocenters. The processes are postulated to proceed via a stereodefined chiral Ir-enolate, which arises upon heteroarene directed enolization of the heteroaryl acetate precursor. The method can be classified as an enantioselective decarboxylative C(sp 3 )–C(sp 3 ) cross-coupling. |
| Author | Bower, John F. Jing, Changcheng Mao, Wenbin |
| AuthorAffiliation | Department of Chemistry University of Liverpool |
| AuthorAffiliation_xml | – name: University of Liverpool – name: Department of Chemistry |
| Author_xml | – sequence: 1 givenname: Changcheng surname: Jing fullname: Jing, Changcheng – sequence: 2 givenname: Wenbin orcidid: 0000-0001-8746-1616 surname: Mao fullname: Mao, Wenbin – sequence: 3 givenname: John F. orcidid: 0000-0002-7551-8221 surname: Bower fullname: Bower, John F. email: john.bower@liverpool.ac.uk |
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| Cites_doi | 10.1021/jacs.9b12320 10.1021/jacs.1c13482 10.1002/ajoc.201800257 10.1021/acs.joc.2c02599 10.1055/s-0028-1088213 10.1002/anie.201900301 10.1021/ja205523e 10.1021/jacs.2c07477 10.1021/jacs.8b00641 10.1021/jo402414k 10.1021/acs.orglett.2c02733 10.1021/jacs.8b04627 10.1055/a-1672-6284 10.1002/chem.201202093 10.1021/ja904441a 10.1002/chem.201604962 10.1021/acs.chemrev.6b00574 10.1002/anie.202107331 10.1055/s-0037-1610315 10.1055/s-0040-1720406 10.1021/jacs.6b01591 10.1021/acs.organomet.2c00032 10.1039/d0cs00359j 10.1021/jacs.5b11335 10.1021/jacs.7b12824 10.1021/cr020040g 10.1246/cl.150913 10.1021/acs.chemrev.5b00695 10.1021/acs.chemrev.0c00559 10.1021/jacs.7b08581 10.1021/jacs.1c06637 10.1021/ja806781u 10.1021/acs.orglett.8b03975 10.1021/acs.orglett.1c02823 10.1021/cs400066q 10.1021/ja060999b 10.1002/anie.201508983 10.1021/acs.orglett.0c02291 10.1002/anie.201702286 10.1039/d2cc04642c 10.1021/jo00395a032 10.1039/D0CS00359J 10.1039/D2CC04642C |
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| Keywords | ETHERS ACETAMIDES ALKYLATION H CONJUGATE ADDITION ALLYLATION HYDROARYLATION C-H ASYMMETRIC HYDROVINYLATION UNACTIVATED ALKENES HYDRIDE |
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| Snippet | Upon exposure to a cationic Ir(I)-complex modified with the chiral diphosphine DuanPhos, hydroalkylations of styrenes and α-olefins with diverse heteroaryl... Upon exposure to a cationic Ir(I)-complex modified with the chiral diphosphine DuanPhos, hydroalkylations of styrenes and alpha-olefins with diverse heteroaryl... Upon exposure to a cationic Ir(I)-complex modified with the chiral diphosphine DuanPhos, hydroalkylations of styrenes and α-olefins with diverse heteroaryl... Upon exposure to a cationic Ir(I)-complex modified with the chiral diphosphine DuanPhos, hydroalkylations of styrenes and α-olefins with diverse heteroaryl... |
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| SubjectTerms | Chemistry Chemistry, Multidisciplinary Communication Physical Sciences Science & Technology |
| Title | Iridium-Catalyzed Enantioselective Alkene Hydroalkylation via a Heteroaryl-Directed Enolization–Decarboxylation Sequence |
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