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Org Lett. 2013 Sep 20;15(18):4814-7. doi: 10.1021/ol402210a. Epub 2013 Sep 9.

Pd-catalyzed Heck-type cascade reactions with N-tosyl hydrazones: an efficient way to alkenes via in situ generated alkylpalladium.

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  • 1Department of Chemistry, University of Science and Technology of China , 96 Jinzhai Road, Hefei, Anhui 230026, People's Republic of China.

Abstract

A palladium-catalyzed Heck-type cascade reaction of aryl halides and N-tosyl hydrazones is reported. The neopentylpalladium species, generated from an intramolecular Heck-type insertion reaction of aryl halides, could efficiently react with carbenes to form highly functionalized alkenes. The synthesis of spiro compounds was also explored via a multiple Heck-type insertion reaction with N-tosyl hydrazone.

PMID:
24016386
[PubMed]
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