Charge Separation in Metal‐Organic Framework Enables Heterogeneous Thiol Catalysis

Author:

Cheng Shengxian1,Ouyang Jing1,Li Muqing2,Diao Yingxue2,Yao Jiachen1,Li Fengxing1,Lee Yat‐For1,SUNG Herman Ho‐Yung1,Williams Ian1,Xu Zhengtao23,Quan Yangjian1ORCID

Affiliation:

1. Department of Chemistry The Hong Kong University of Science and Technology Clear Water Bay Hong Kong China

2. Department of Chemistry City University of Hong Kong 83 Tat Chee Avenue Kowloon, Hong Kong China

3. Institute of Materials Research and Engineering (IMRE) Agency of Science Technology and Research (A*STAR) 2 Fusionopolis Way Singapore 138634 Singapore

Abstract

AbstractPhotoinduced metal–organic framework (MOF) enabled heterogeneous thiol catalysis has been achieved for the first time. MOF Zr‐TPDCS‐1, consisting of Zr6‐clusters and TPDCS linkers (TPDCS=3,3′′,5,5′′‐tetramercapto[1,1′:4′,1′′‐terphenyl]‐4,4′′‐dicarboxylate), effectively catalyzed the borylation, silylation, phosphorylation, and thiolation of organic molecules. Upon irradiation, the fast electron transfer from TPDCS to Zr6‐cluster is believed to facilitate the formation of the thiyl radical, a hydrogen atom transfer catalyst, which competently abstracts the hydrogen from borane, silane, phosphine, or thiol for generating the corresponding element radical to engender the chemical transformations. The elaborate control experiments evidenced the generation of thiyl radicals in MOF and illustrated a radical reaction pathway. The gram‐scale reaction worked well, and the product was conveniently separated via centrifugation and vacuum with a turnover number (TON) of ≈3880, highlighting the practical application potential of heterogeneous thiyl‐radical catalysis.

Publisher

Wiley

Subject

General Chemistry,Catalysis

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