Journal
ORGANIC CHEMISTRY FRONTIERS
Volume 9, Issue 23, Pages 6490-6497Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/d2qo01317g
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Funding
- National Science Foundation of China [22001051]
- Hangzhou Leading Innovation and Entrepreneurship Team Project [TD2020015]
- Hangzhou Normal University
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A highly efficient cross-electrophile coupling of organic halides with thiol-free synthesized N-thiophthalimides as direct thiolating surrogates was presented. This strategy avoids the use of odorous and toxic thiols and features low catalyst loading, good functional group tolerance, and diverse downstream synthesis.
Unsymmetrical sulfides are widely found in the pharmaceutical industry, organic synthesis, and materials science. As a result, it will be of great significance to discover mild and efficient methodologies and electrophilic sulfur transfer reagents, avoiding the general employment of odorous and toxic thiols. Herein, we present a highly efficient nickel-catalyzed cross-electrophile coupling of organic halides with thiol-free synthesized N-thiophthalimides as direct thiolating surrogates. This practical strategy features extremely low catalyst loading, good functional group tolerance and diverse downstream synthesis, enabling the construction of a broad range of sulfides under base-free conditions. Notably, a modified and more efficient reductive thiolation of disulfides was developed by employing our mild reaction conditions.
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