Copper‐Enabled Photo‐Sulfonylation of Aryl Halides Using Alkylsulfinates

Author:

Mdluli Velabo1ORCID,Lehnherr Dan1ORCID,Lam Yu‐hong2ORCID,Ji Yining3,Newman Justin A.3,Kim Jungchul1

Affiliation:

1. Process Research and Development Merck & Co., Inc. Rahway New Jersey 07065 United States

2. Modeling and Informatics Merck & Co., Inc. Rahway New Jersey 07065 United States

3. Analytical Research and Development Merck & Co., Inc. Rahway New Jersey 07065 United States

Abstract

AbstractA photochemical synthetic method to access sulfones from aryl halides and sodium alkylsulfinates in the presence of CuCl is reported. Regio‐ and chemoselectivity for the sulfonylation is observed for polyhalogenated arenes. Mechanistic studies indicate that a copper sulfinate reagent is formed in situ from CuCl and sodium sulfinate based on NMR experiments. Potential reaction intermediates, including excited state aryl halides are studied using density functional theory calculations and reveal energetically accessible non‐planar triplet geometries.

Publisher

Wiley

Subject

General Chemistry

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1. Overview of Recent Scale-Ups in Organic Electrosynthesis (2000–2023);Organic Process Research & Development;2024-01-18

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