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Synlett 2018; 29(16): 2081-2086
DOI: 10.1055/s-0037-1610161
DOI: 10.1055/s-0037-1610161
synpacts
A High-Throughput Approach to Discovery: Heck-Type Reactivity with Aldehydes
This work was supported by the University of Ottawa, the Natural Sciences and Engineering Research Council of Canada (NSERC) and the Canada Research Chairs program.Further Information
Publication History
Received: 27 March 2018
Accepted after revision: 26 April 2018
Publication Date:
12 June 2018 (online)
Abstract
The classical Heck reaction is among the most powerful methods available for the construction of C–C bonds. Modification of this transformation to utilize diverse organohalide coupling partners has resulted in new reactions such as the silyl-Heck, aza-Heck, and boryl-Heck reactions. In contrast, modification of the olefin coupling partner is rare. For instance, use of the π-bond of an aldehyde instead of an alkene would provide ketones via a carbonyl-Heck process. This seemingly minor manipulation of the Heck reaction has proven surprisingly difficult to realize in practice. Through the use of high-throughput experimentation techniques, an efficient catalyst system for this transformation was identified, enabling the intermolecular coupling of organotriflates and aldehydes to synthesize diverse ketones.
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