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An Overview of Recent Advances in the Synthesis of Organic Unsymmetrical Disulfides
Authors:Chiu Ling Ong  Salam Titinchi  Joon Ching Juan  Nader Ghaffari Khaligh
Affiliation:1. Nanotechnology and Catalysis Research Center, Institute for Advanced Studies (IAS), University of Malaya, 50603 Kuala Lumpur, Malaysia;2. Department of Chemistry, University of the Western Cape, Bellville, Cape Town, 7535 South Africa
Abstract:Organic unsymmetrical disulfides have been extensively applied in various academic and industrial fields including intermediates in organic synthesis, agriculture, and food science, natural materials, biochemistry, pharmaceutical and medicine chemistry, polymers, material engineering, etc. They play a crucial role in the fabrication of various biological active sulfur heterocycles. Due to broad and extensive applications, many methods have been developed for the synthesis of unsymmetrical S−S and efforts have been made to improve some issues such as cost, energy efficiency, green chemistry, avoid or minimizing waste generation. Several outstanding review articles have been previously published highlighting the advances of S−S bond formation, in general, using various reagents under different conditions in the absence or presence of oxidants/catalysts. In 2020, a review paper was published by our group focusing on recent developments since 2014 in the synthesis of organic symmetrical disulfides. However, investigations on new catalytic methods are being regularly reported and new types of unsymmetrical disulfides are synthesized. The present overview has attempted to systematically summarize recent advances in the process of unsymmetrical S−S bond formation with a major focus since 2010, highlighting mechanistic considerations, substrate scope, advantages, and limitations. The patents are not studied in this overview.
Keywords:asymmetric synthesis  cross-coupling  organic unsymmetrical disulfides  oxidative cross-coupling  photocatalytic coupling  thiol-disulfide exchange  mechanism
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