Photocatalytic Cleavage of Trityl Protected Thiols and Alcohols

Author:

Murakami Sho12,Brudy Cosima1,Pieber Bartholomäus1ORCID,Bachmann Moritz1,Takemoto Yoshiji2

Affiliation:

1. Department of Biomolecular Systems, Max-Planck-Institute of Colloids and Interfaces

2. Graduate School of Pharmaceutical Sciences, Kyoto University

Abstract

AbstractWe report the visible light photocatalytic cleavage of trityl thioethers or ethers under pH-neutral conditions. The method results in the formation of the respective symmetrical disulfides and alcohols in moderate to excellent yield. The protocol only requires the addition of a suitable photocatalyst and light rendering it orthogonal to several functionalities, including acid labile protective groups. The same conditions can be used to directly convert trityl-protected thiols into unsymmetrical disulfides or selenosulfides, and to cleave trityl resins in solid phase organic synthesis.

Funder

Japan Society for the Promotion of Science

Boehringer Ingelheim Foundation

Max-Planck Society

Publisher

Georg Thieme Verlag KG

Subject

Organic Chemistry,Catalysis

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