Journal
ACS CATALYSIS
Volume 12, Issue 21, Pages 13435-13445Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acscatal.2c0318713435
Keywords
KEYWORDS; asymmetric remote C; H activation; ligand-controlled; meta -selective; olefination; arylation; palladium catalysis
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Funding
- NSFC [22022111, 21978272, 22071248]
- Natural Science Foundation of Fujian Province [2020J02008, 2020J01108]
- Fundamental Research Funds for the Provincial Universities of Zhejiang [RF-B2020006]
- Province -Ministry Co-Construct State Key Laboratory of Green Chemistry -Synthesis Technology at Zhejiang University of Technology
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The use of a chiral ligand-controlled, asymmetric remote meta-C-H activation enables asymmetric C-H olefination and arylation of hydrocinnamic acid derivatives. The origins of the enantioselectivity were explained using density functional theory calculations.
The use of a chiral ligand for stereocontrol has assisted the development of a number of asymmetric functionalization of proximal C-H bonds. Herein, we report a chiral ligand-controlled, asymmetric remote meta-C-H activation of arenes, leading to asymmetric C-H olefination and arylation of hydrocinnamic acid derivatives through desymmetrization with Ac-L-Phe-OH as the chiral ligand using a Pd(II) catalyst. The origins of the enantioselectivity were explained with density functional theory calculations. The larger distortion energy of the substrate part in the C-H bond activation transition structure S-TS1 is the major controlling factor that disfavors the formation of the S-enantiomer product.
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