Deoxygenative Transformation of Alcohols via Phosphoranyl Radical from Exogenous Radical Addition

Author:

Xu Wenhao1,Fan Chao2,Hu Xile2ORCID,XU Tao1ORCID

Affiliation:

1. Shanghai Key Laboratory of Chemical Assessment and Sustain-ability School of Chemical Science and Engineering Tongji University 1239 Siping Road 200092 Shanghai P. R. China

2. Laboratory of Inorganic Synthesis and Catalysis Institute of Chemical Sciences and Engineering Ecole Polytechnique Fédérale de Lausanne (EPFL) CH-1015 Lausanne Switzerland

Abstract

AbstractA general approach to the direct deoxygenative transformation of primary, secondary, and tertiary alcohols has been developed. It undergoes through phosphoranyl radical intermediates generated by the addition of exogenous iodine radical to trivalent alkoxylphosphanes. Since these alkoxylphosphanes are readily in situ obtained from alcohols and commercially available, inexpensive chlorodiphenylphosphine, a diverse range of alcohols with various functional groups can be utilized to proceed deoxygenative cross‐couplings with alkenes or aryl iodides. The selective transformation of polyhydroxy substrates and the rapid synthesis of complex organic molecules are also demonstrated with this method.

Funder

École Polytechnique Fédérale de Lausanne

Publisher

Wiley

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