Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 143, Issue 1, Pages 114-120Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.0c11735
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Funding
- National Key R&D Program of China [2016YFA0202900]
- NSFC [21821002, 91856201, 21961132002]
- CAS [XDB20000000, QYZDY-SSW-SLH012]
- Science and Technology Commission of Shanghai Municipality [18JC1411302, 19590750400]
- Initiative Postdocs Supporting Program [BX20180342]
- China Postdoctoral Science Foundation [2019M650092]
- Pharmaron
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This study reveals a rhodium(III)-catalyzed enantioselective C-H activation/annulation process for the synthesis of chiral azoniahelicenes with high yields and enantioselectivity. Mechanistic studies suggest that C-H bond cleavage may be the turnover-limiting step.
A rhodium(III)-catalyzed enantioselective C-H activation/annulation process is disclosed. With a catalyst derived from a chiral CpRh(III) complex and a chiral acid, the direct annulation reactions between 1-aryl isoquinoline derivatives and alkynes take place smoothly to afford a series of chiral azoniahelicenes in excellent yields and enantioselectivity (up to 99% yield and 96% ee). Mechanistic studies suggest that C-H bond cleavage may be the turnover-limiting step.
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