Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 59, Issue 24, Pages 9594-9600Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202000532
Keywords
arylation; C-H activation; palladium; pyridone ligands; transient directing groups
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Funding
- Scripps Research Institute, NIH (NIGMS) [R01 GM084019]
- Bristol-Myers Squibb
- Jiangsu Industrial Technology Research Institute (JITRI)
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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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