Construction of Axial Chirality by Rhodium-Catalyzed Asymmetric Dehydrogenative Heck Coupling of Biaryl Compounds with Alkenes
Enantioselective construction of axially chiral biaryls by direct CH bond functionalization reactions has been realized. Novel axially chiral biaryls were synthesized by the direct CH bond olefination of biaryl compounds, using a chiral [Cp*RhIII] catalyst, in good to excellent yields and enantios...
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| Published in | Angewandte Chemie International Edition Vol. 53; no. 48; pp. 13244 - 13247 |
|---|---|
| Main Authors | , |
| Format | Journal Article |
| Language | English |
| Published |
Weinheim
WILEY-VCH Verlag
24.11.2014
WILEY‐VCH Verlag Wiley Wiley Subscription Services, Inc |
| Edition | International ed. in English |
| Subjects | |
| Online Access | Get full text |
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| Abstract | Enantioselective construction of axially chiral biaryls by direct CH bond functionalization reactions has been realized. Novel axially chiral biaryls were synthesized by the direct CH bond olefination of biaryl compounds, using a chiral [Cp*RhIII] catalyst, in good to excellent yields and enantioselectivities. The obtained axially chiral biaryls were found as suitable ligands for rhodium‐catalyzed asymmetric conjugate additions.
An axe to grind? Novel axially chiral biaryls were synthesized by the direct CH bond olefination of biaryl compounds, using a chiral [Cp*RhIII] catalyst (1), in good to excellent yields and enantioselectivities. The biaryls were found as suitable ligands for rhodium‐catalyzed asymmetric conjugate addition reactions. |
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| AbstractList | Enantioselective construction of axially chiral biaryls by direct C-H bond functionalization reactions has been realized. Novel axially chiral biaryls were synthesized by the direct C-H bond olefination of biaryl compounds, using a chiral [Cp*Rh(III)] catalyst, in good to excellent yields and enantioselectivities. The obtained axially chiral biaryls were found as suitable ligands for rhodium-catalyzed asymmetric conjugate additions. Enantioselective construction of axially chiral biaryls by direct C-H bond functionalization reactions has been realized. Novel axially chiral biaryls were synthesized by the direct C-H bond olefination of biaryl compounds, using a chiral [Cp*Rh(III)] catalyst, in good to excellent yields and enantioselectivities. The obtained axially chiral biaryls were found as suitable ligands for rhodium-catalyzed asymmetric conjugate additions.Enantioselective construction of axially chiral biaryls by direct C-H bond functionalization reactions has been realized. Novel axially chiral biaryls were synthesized by the direct C-H bond olefination of biaryl compounds, using a chiral [Cp*Rh(III)] catalyst, in good to excellent yields and enantioselectivities. The obtained axially chiral biaryls were found as suitable ligands for rhodium-catalyzed asymmetric conjugate additions. Enantioselective construction of axially chiral biaryls by direct CH bond functionalization reactions has been realized. Novel axially chiral biaryls were synthesized by the direct CH bond olefination of biaryl compounds, using a chiral [Cp*Rh III ] catalyst, in good to excellent yields and enantioselectivities. The obtained axially chiral biaryls were found as suitable ligands for rhodium‐catalyzed asymmetric conjugate additions. Enantioselective construction of axially chiral biaryls by direct C--H bond functionalization reactions has been realized. Novel axially chiral biaryls were synthesized by the direct C--H bond olefination of biaryl compounds, using a chiral [Cp*Rh super(III)] catalyst, in good to excellent yields and enantioselectivities. The obtained axially chiral biaryls were found as suitable ligands for rhodium-catalyzed asymmetric conjugate additions. An axe to grind? Novel axially chiral biaryls were synthesized by the direct C--H bond olefination of biaryl compounds, using a chiral [Cp*Rh super(III)] catalyst (1), in good to excellent yields and enantioselectivities. The biaryls were found as suitable ligands for rhodium-catalyzed asymmetric conjugate addition reactions. Enantioselective construction of axially chiral biaryls by direct CH bond functionalization reactions has been realized. Novel axially chiral biaryls were synthesized by the direct CH bond olefination of biaryl compounds, using a chiral [Cp*RhIII] catalyst, in good to excellent yields and enantioselectivities. The obtained axially chiral biaryls were found as suitable ligands for rhodium‐catalyzed asymmetric conjugate additions. An axe to grind? Novel axially chiral biaryls were synthesized by the direct CH bond olefination of biaryl compounds, using a chiral [Cp*RhIII] catalyst (1), in good to excellent yields and enantioselectivities. The biaryls were found as suitable ligands for rhodium‐catalyzed asymmetric conjugate addition reactions. Enantioselective construction of axially chiral biaryls by direct CH bond functionalization reactions has been realized. Novel axially chiral biaryls were synthesized by the direct CH bond olefination of biaryl compounds, using a chiral [Cp*RhIII] catalyst, in good to excellent yields and enantioselectivities. The obtained axially chiral biaryls were found as suitable ligands for rhodium-catalyzed asymmetric conjugate additions. |
| Author | You, Shu-Li Zheng, Jun |
| Author_xml | – sequence: 1 givenname: Jun surname: Zheng fullname: Zheng, Jun organization: State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032 (China) http://shuliyou.sioc.ac.cn/ – sequence: 2 givenname: Shu-Li surname: You fullname: You, Shu-Li email: slyou@sioc.ac.cn organization: State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032 (China) http://shuliyou.sioc.ac.cn/ |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/25346171$$D View this record in MEDLINE/PubMed |
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| Copyright | 2014 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim. 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim |
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| GrantInformation_xml | – fundername: National Basic Research Program of China funderid: 2015CB856600 – fundername: National Natural Science Foundation of China funderid: 21025209; 21121062; 21332009 – fundername: National Natural Science Foundation of China; National Natural Science Foundation of China (NSFC) grantid: 21025209; 21121062; 21332009 – fundername: National Basic Research Program of China (973 Program); National Basic Research Program of China grantid: 2015CB856600 |
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| ISSN | 1433-7851 1521-3773 |
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| Issue | 48 |
| Keywords | ACTIVATION C-H BOND chirality NATURAL-PRODUCTS asymmetric catalysis 2+2+2 CYCLOADDITION OLEFIN LIGANDS FUNCTIONALIZATION 2,2',6,6'-TETRAHYDROXYBIPHENYL C-H activation biaryls 2-NAPHTHOLS DIENE LIGANDS rhodium OXOVANADIUM(IV) COMPLEXES CH activation |
| Language | English |
| License | http://onlinelibrary.wiley.com/termsAndConditions#vor 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim. |
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| Notes | National Natural Science Foundation of China - No. 21025209; No. 21121062; No. 21332009 ArticleID:ANIE201408805 We thank the National Basic Research Program of China (973 Program 2015CB856600) and the National Natural Science Foundation of China (21025209, 21121062, and 21332009) for generous financial support. ark:/67375/WNG-H4BN08G1-9 National Basic Research Program of China - No. 2015CB856600 istex:E8F9D27068EFA7AE3893763C154F6E0B6EA80FA0 ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 14 content type line 23 |
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| PublicationDate | November 24, 2014 |
| PublicationDateYYYYMMDD | 2014-11-24 |
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| PublicationPlace | Weinheim |
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| PublicationTitle | Angewandte Chemie International Edition |
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| PublicationYear | 2014 |
| Publisher | WILEY-VCH Verlag WILEY‐VCH Verlag Wiley Wiley Subscription Services, Inc |
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| Snippet | Enantioselective construction of axially chiral biaryls by direct CH bond functionalization reactions has been realized. Novel axially chiral biaryls were... Enantioselective construction of axially chiral biaryls by direct C-H bond functionalization reactions has been realized. Novel axially chiral biaryls were... Enantioselective construction of axially chiral biaryls by direct CH bond functionalization reactions has been realized. Novel axially chiral biaryls were... Enantioselective construction of axially chiral biaryls by direct C--H bond functionalization reactions has been realized. Novel axially chiral biaryls were... |
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| SubjectTerms | Alkenes Alkenes - chemistry asymmetric catalysis Asymmetry biaryls Bonding Catalysis Catalysts Chemistry Chemistry, Multidisciplinary Chirality Conjugates Construction Cyclization CH activation Joining Ligands Models, Molecular Physical Sciences Rhodium Rhodium - chemistry Science & Technology Stereoisomerism |
| Title | Construction of Axial Chirality by Rhodium-Catalyzed Asymmetric Dehydrogenative Heck Coupling of Biaryl Compounds with Alkenes |
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