Four-Component Radical Dual Difunctionalization (RDD) of Two Different Alkenes with Aldehydes and tert-Butyl Hydroperoxide (TBHP): An Easy Access to β,δ-Functionalized Ketones

Chuan-Shuo Wu; Ren-Xiang Liu; Da-You Ma; Cui-Ping Luo; Luo Yang

doi:10.1021/acs.orglett.9b02264

Four-Component Radical Dual Difunctionalization (RDD) of Two Different Alkenes with Aldehydes and tert-Butyl Hydroperoxide (TBHP): An Easy Access to β,δ-Functionalized Ketones

Org Lett. 2019 Aug 2;21(15):6117-6121. doi: 10.1021/acs.orglett.9b02264. Epub 2019 Jul 19.

Authors

Chuan-Shuo Wu¹, Ren-Xiang Liu¹, Da-You Ma², Cui-Ping Luo¹, Luo Yang¹

Affiliations

¹ Key Laboratory for Green Organic Synthesis and Application of Hunan Province, College of Chemistry , Xiangtan University , Hunan 411105 , P. R. China.
² Xiangya School of Pharmaceutical Sciences , Central South University , Hunan 410013 , P. R. China.

PMID: 31322353
DOI: 10.1021/acs.orglett.9b02264

Abstract

A convenient Fe-catalyzed four-component radical dual difunctionalization and ordered assembly of two alkenes with aromatic/aliphatic aldehydes and TBHP to provide chain elongated β,δ-functionalized ketones via a one-pot procedure has been developed. Aldehydes were homolytically cleavaged to produce acyl radicals and subsequently allowed for the successive construction of C(sp²)-C(sp³), C(sp³)-C(sp³), and C(sp³)-O bonds via dual radical insertions and radical-radical coupling, following the intrinsic nucleo/electrophilic reactivity of both the radicals and alkenes.

Publication types

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