期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 60, 期 41, 页码 22184-22188出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202107139
关键词
3-nitroindole; allylic substitution; dearomatization; diastereoselectivity; palladium
资金
- MOST [2016YFA0202900]
- NSFC [21821002, 22031012, 21961132002]
A novel Pd-catalyzed method for dearomative methoxyallylation of 3-nitroindoles with allyl carbonates has been developed, achieving high yields and diastereoselectivity. The method demonstrates good scalability and practicality with relatively low catalyst loading. Kinetic experiments suggest that the nucleophilic attack of the alkoxide anion is the rate-determining step in this reaction.
Herein we report a Pd-catalyzed dearomative methoxyallylation of 3-nitroindoles with readily available allyl carbonates. Good yields (up to 86 %) and diastereoselectivity (up to >20:1 dr) are obtained for a wide range of substrates. The compatibility of gram-scale synthesis and the relatively low catalyst loading (down to 1 mol % of [Pd]) enhance the practicality of this method. The kinetic experiments indicate that the rate-determining step of this reaction is the nucleophilic attack of the alkoxide anion.
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