Angewandte Chemie - International Edition
Angewandte Chemie - International Edition
5 years ago

Base-Controlled Completely Selective Linear or Branched Rhodium(I)-Catalyzed C−H ortho-Alkylation of Azines without Preactivation

Base-Controlled Completely Selective Linear or Branched Rhodium(I)-Catalyzed C−H ortho-Alkylation of Azines without Preactivation
Gaël Tran, Kevin D. Hesp, Jonathan A. Ellman, Vincent Mascitti
A [RhI]/bisphosphine/base catalytic system for the ortho-selective C−H alkylation of azines by acrylates and acrylamides is reported. This catalytic system features an unprecedented complete linear or branched selectivity that is solely dependent on the catalytic base that is used. Complete branched selectivity is even achieved for ethyl methacrylate, which enables the introduction of a quaternary carbon center. Excellent functional group compatibility is demonstrated for both linear and branched alkylations. The operational simplicity and broad scope of this transformation allow for rapid access to functionalized azines of direct pharmaceutical and agrochemical relevance. A basic choice: The linear/branched selectivity of an ortho-selective C−H alkylation of azines without preactivation is completely controlled by a simple switch between base catalysts. Under the “branched” conditions even quaternary carbon centers can be introduced. Excellent functional group compatibility is demonstrated for both linear and branched alkylations with acrylate derivatives.

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

DOI: 10.1002/anie.201702409

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