N-Heterocyclic Carbene-Catalyzed Olefination of Aldehydes with Vinyliodonium Salts To Generate α,β-Unsaturated Ketones

Adam A Rajkiewicz; Marcin Kalek

doi:10.1021/acs.orglett.8b00447

N-Heterocyclic Carbene-Catalyzed Olefination of Aldehydes with Vinyliodonium Salts To Generate α,β-Unsaturated Ketones

Org Lett. 2018 Apr 6;20(7):1906-1909. doi: 10.1021/acs.orglett.8b00447. Epub 2018 Mar 14.

Authors

Adam A Rajkiewicz^{1

2}, Marcin Kalek¹

Affiliations

¹ Centre of New Technologies , University of Warsaw , Banacha 2C , 02-097 Warsaw , Poland.
² Faculty of Chemistry , University of Warsaw , Pasteura 1 , 02-093 Warsaw , Poland.

PMID: 29537278
DOI: 10.1021/acs.orglett.8b00447

Abstract

An organocatalyzed metal-free, direct olefination of aldehydes with vinyliodonium salts has been achieved by an N-heterocyclic carbene-promoted C-H bond activation. The reaction proceeds under very mild conditions, delivering a range of (hetero)aryl-vinyl ketones in good yields. The retention of the double bond configuration is uniformly observed, and the application of 2-methoxyphenyl auxiliary group in iodonium salts secures a complete selectivity of the vinyl transfer.

Publication types

Research Support, Non-U.S. Gov't