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Synlett 2014; 25(11): 1621-1625
DOI: 10.1055/s-0033-1341279
DOI: 10.1055/s-0033-1341279
letter
Nickel-Catalyzed sp3 C–H Bond Activation from Decarboxylative CrossCoupling of α,β-Unsaturated Carboxylic Acids with Amides
Authors
Further Information
Publication History
Received: 10 March 2014
Accepted after revision: 07 April 2014
Publication Date:
14 May 2014 (online)
Abstract
Nickel-catalyzed functionalization of C(sp3)–H bonds adjacent to a nitrogen atom in amides through decarboxylative cross-coupling of α,β-unsaturated carboxylic acids is reported. A possible reaction mechanism is proposed that involves radical intermediate species.
Primary Data
- for this article are available online at http://www.thieme-connect.com/products/ejournals/journal/
10.1055/s-00000083 and can be cited using the following DOI: 10.4125/pd0058th.
- Primary Data (ZIP)
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- 19 Typical Procedure: To a mixture of cinnamic acid (0.148 g, 1 mmol), Ni(OAc)2·4H2O (25 mg, 0.1 mmol), and N,N-dimethylacetamide (2 mL), tert-butyl hydroperoxide (0.39 g, 3 mmol, 70% in water) was added at r.t. dropwise. The resulting mixture was heated to 100 °C for 16 h, then the mixture was added to dichloromethane (40 mL) and washed with water and saturated brine. The organic solution was dried with anhydrous magnesium sulfate and the desired product was separated on a silica gel column (petroleum ether–EtOAc).