Pd-II-Catalyzed Enantioselective C(sp(3))-H Arylation of Cyclobutyl Ketones Using a Chiral Transient Directing Group
The use of chiral transient directing groups (TDGs) is a promising approach for developing Pd-II-catalyzed enantioselective C(sp(3))-H activation reactions. However, this strategy is challenging because the stereogenic center on the TDG is often far from the C-H bond, and both TDG covalently attache...
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| Published in | Angewandte Chemie International Edition Vol. 59; no. 24; pp. 9594 - 9600 |
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| Main Authors | , , , , , , |
| Format | Journal Article |
| Language | English |
| Published |
WEINHEIM
Wiley
08.06.2020
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| Subjects | |
| Online Access | Get full text |
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| Abstract | The use of chiral transient directing groups (TDGs) is a promising approach for developing Pd-II-catalyzed enantioselective C(sp(3))-H activation reactions. However, this strategy is challenging because the stereogenic center on the TDG is often far from the C-H bond, and both TDG covalently attached to the substrate and free TDG are capable of coordinating to Pd-II centers, which can result in a mixture of reactive complexes. We report a Pd-II-catalyzed enantioselective beta-C(sp(3))-H arylation reaction of aliphatic ketones using a chiral TDG. A chiral trisubstituted cyclobutane was efficiently synthesized from a mono-substituted cyclobutane through sequential C-H arylation reactions, thus demonstrating the utility of this method for accessing structurally complex products from simple starting materials. The use of an electron-deficient pyridone ligand is crucial for the observed enantioselectivity. Interestingly, employing different silver salts can reverse the enantioselectivity. |
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| AbstractList | The use of chiral transient directing groups (TDGs) is a promising approach for developing Pd
-catalyzed enantioselective C(sp
)-H activation reactions. However, this strategy is challenging because the stereogenic center on the TDG is often far from the C-H bond, and both TDG covalently attached to the substrate and free TDG are capable of coordinating to Pd
centers, which can result in a mixture of reactive complexes. We report a Pd
-catalyzed enantioselective β-C(sp
)-H arylation reaction of aliphatic ketones using a chiral TDG. A chiral trisubstituted cyclobutane was efficiently synthesized from a mono-substituted cyclobutane through sequential C-H arylation reactions, thus demonstrating the utility of this method for accessing structurally complex products from simple starting materials. The use of an electron-deficient pyridone ligand is crucial for the observed enantioselectivity. Interestingly, employing different silver salts can reverse the enantioselectivity. The use of chiral transient directing groups (TDGs) is a promising approach for developing Pd-II-catalyzed enantioselective C(sp(3))-H activation reactions. However, this strategy is challenging because the stereogenic center on the TDG is often far from the C-H bond, and both TDG covalently attached to the substrate and free TDG are capable of coordinating to Pd-II centers, which can result in a mixture of reactive complexes. We report a Pd-II-catalyzed enantioselective beta-C(sp(3))-H arylation reaction of aliphatic ketones using a chiral TDG. A chiral trisubstituted cyclobutane was efficiently synthesized from a mono-substituted cyclobutane through sequential C-H arylation reactions, thus demonstrating the utility of this method for accessing structurally complex products from simple starting materials. The use of an electron-deficient pyridone ligand is crucial for the observed enantioselectivity. Interestingly, employing different silver salts can reverse the enantioselectivity. Abstract The use of chiral transient directing groups (TDGs) is a promising approach for developing Pd II ‐catalyzed enantioselective C(sp 3 )−H activation reactions. However, this strategy is challenging because the stereogenic center on the TDG is often far from the C−H bond, and both TDG covalently attached to the substrate and free TDG are capable of coordinating to Pd II centers, which can result in a mixture of reactive complexes. We report a Pd II ‐catalyzed enantioselective β‐C( sp 3 )−H arylation reaction of aliphatic ketones using a chiral TDG. A chiral trisubstituted cyclobutane was efficiently synthesized from a mono‐substituted cyclobutane through sequential C−H arylation reactions, thus demonstrating the utility of this method for accessing structurally complex products from simple starting materials. The use of an electron‐deficient pyridone ligand is crucial for the observed enantioselectivity. Interestingly, employing different silver salts can reverse the enantioselectivity. |
| Author | Xiao, Li-Jun Hong, Kai Yeung, Kap-Sun Ewing, William R. Hu, Liang Luo, Fan Yu, Jin-Quan |
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| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/32155313$$D View this record in MEDLINE/PubMed |
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| Keywords | ACTIVATION INDOLINES ALDEHYDES arylation DESYMMETRIZATION FUNCTIONALIZATION transient directing groups C-H activation C-H ARYLATION AMINES BONDS CONSTRUCTION pyridone ligands palladium C(SP)-H C−H activation |
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| Snippet | The use of chiral transient directing groups (TDGs) is a promising approach for developing Pd-II-catalyzed enantioselective C(sp(3))-H activation reactions.... The use of chiral transient directing groups (TDGs) is a promising approach for developing Pd -catalyzed enantioselective C(sp )-H activation reactions.... Abstract The use of chiral transient directing groups (TDGs) is a promising approach for developing Pd II ‐catalyzed enantioselective C(sp 3 )−H activation... |
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| SubjectTerms | Benzene - chemistry Catalysis Chemistry Chemistry, Multidisciplinary Cyclobutanes - chemistry Electron Transport Ketones - chemistry Palladium - chemistry Physical Sciences Science & Technology Stereoisomerism |
| Title | Pd-II-Catalyzed Enantioselective C(sp(3))-H Arylation of Cyclobutyl Ketones Using a Chiral Transient Directing Group |
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