Accessing and Utilizing Thiols in Organic Chemistry

Thiols (mercaptans) are a versatile and indispensable class of organosulfur compounds in organic chemistry, known for their redox properties, nucleophilicity, and ability to form strong bonds with metals. They find application across several fields including synthesis, catalysis, chemical biology, and materials science. Despite these considerations, synthetic methodology towards thiols is not necessarily prioritized, and existing work in this area is seldom at the forefront. This review highlights a few of the significant instances of thiol-based chemistry and then provides an overview of strategies to synthesize them. While direct methods are presented, emphasis is placed on the concept of “masked thiols” as accessible yet inconspicuous thiol precursors, organized by structural class and the common procedures to “unmask” them. Additionally, a section on diversification demonstrates the foundational synthetic utility thiols have in reaching other sulfur-containing functional groups.