European Journal of Organic Chemistry
European Journal of Organic Chemistry
5 years ago

Tandem O–H Insertion/[3,3]-Sigmatropic Rearrangement of Rhodium Carbenoids with 2-Furfuryl Alcohols: A Strategy To Access Polysubstituted Furans

Tandem O–H Insertion/[3,3]-Sigmatropic Rearrangement of Rhodium Carbenoids with 2-Furfuryl Alcohols: A Strategy To Access Polysubstituted Furans
Jinna Song, Rui Zhao, Pengbing Mi, Hannan Wang
Polysubstituted furans are versatile building blocks in organic synthesis and are widely spread in a variety of natural products, pharmaceuticals, and functional materials. Herein, we report a convenient, facile, and economic approach for the synthesis of polysubstituted furans through a tandem O–H insertion/[3,3]-sigmatropic rearrangement of rhodium carbenoids with easily available furfuryl alcohols. This protocol is characterized by its operational simplicity, high efficiency with excellent yields, broad substrate scope, and great functional-group tolerance.A convenient, facile, and economic approach for the synthesis of polysubstituted furans through a tandem O–H insertion/[3,3]-sigmatropic rearrangement of rhodium carbenoids with easily available furfuryl alcohols is reported. This protocol is characterized by its operational simplicity, high efficiency with excellent yields, broad substrate scope, and great functional-group tolerance. Ts = tosyl.

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/ejoc.201701217

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