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Synthesis 2016; 48(21): 3719-3729
DOI: 10.1055/s-0035-1561671
DOI: 10.1055/s-0035-1561671
paper
Synthesis of Six- and Seven-Membered Chloromethyl-Substituted Heterocycles via Palladium-Catalyzed Amino- and Oxychlorination
Further Information
Publication History
Received: 15 April 2016
Accepted after revision: 04 May 2016
Publication Date:
21 June 2016 (online)
Dedicated to our friend and former boss Professor Giovanni Poli on the occasion of his 60th birthday
Abstract
The synthesis of six- and seven-membered chloromethyl-substituted heterocycles, such as piperazinone, tetrahydroquinoxaline, benzodiazepinone, and benzoxazepinone, is reported using palladium-catalyzed vicinal diheterofunctionalization of nonactivated alkenes. The reaction conditions for this domino process are soft and mild, and the chloromethyl appendage allows various post-functionalizations via simple nucleophilic substitutions.
Supporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0035-1561671.
- Supporting Information
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For vicinal aminoheterofunctionalization of alkenes catalyzed by metals other than Pd or under metal-free conditions, see: