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Updated: Jun 6, 2025

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
Published on: January 19, 2016
Insight into the Metal-Free Reduction of Isocyanates to N-Methyl Anilines at Room Temperature
Pinaki Nad1, Hemanta K Kisan1, Arup Mukherjee1
1Department of Chemistry, Indian Institute of Technology Bhilai, Durg, Chhattisgarh, 491002, India.
Abstract:
A simple and sustainable protocol has been developed to reduce isocyanates to the N-methyl anilines under metal-free conditions. The reaction proceeds with BF3 ⋅ OEt2 as a catalyst and ammonia borane as a hydrogen source in THF at room temperature, leading to the formation of a wide range of substituted aniline derivatives. Control experiments and deuterium labeling studies were performed to understand the mechanism of the present procedure. A detailed computational study was also conducted to shed light on the possible mechanism and free energies of the intermediates and transition states involved in this present protocol.
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