Transition-Metal-Catalyzed Transformation of Sulfonates via S–O Bond Cleavage: Synthesis of Alkyl Aryl Ether and Diaryl Ether
2019
Chen, Xuemeng | Xiao, Xue | Sun, Haotian | Li, Yue | Cao, Haolin | Zhang, Xuemei | Yang, Shengyong | Lian, Zhong
The catalytic conversion of sulfonates, a versatile class of pharmaceutical intermediates, is usually based on C–O bond cleavage. In this paper, however, we discover a rare transformation of sulfonates via S–O bond cleavage catalyzed by transition metal, through which alkyl sulfonates could undergo an intramolecular desulfitative C–O coupling to form aryl alkyl ethers in the presence of a nickel catalyst. Meanwhile, aryl sulfonates perform similarly to give diaryl ethers catalyzed by a palladium complex. This transformation could tolerate a wide range of functionalities. Controlled experiments reveal that the 2-pyridyl group is necessary to promote the reaction as designed. Crossover experiments proved that this transformation might proceed partly in an intermolecular pathway.
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