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Elemental‐Sulfur‐Enabled Divergent Synthesis of Disulfides, Diselenides, and Polythiophenes from β‐CF 3 ‐1,3‐Enynes
Author(s) -
Jin Shengnan,
Li ShiJun,
Ma Xingxing,
Su Jianke,
Chen Haohua,
Lan Yu,
Song Qiuling
Publication year - 2021
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.202009194
Subject(s) - thiophene , chemistry , annulation , sulfur , substrate (aquarium) , combinatorial chemistry , organic chemistry , catalysis , oceanography , geology
Divergent synthesis for precise constructions of cyclic unsymmetrical diaryl disulfides or diselenides and polythiophenes from CF 3 ‐containing 1,3‐enynes and S 8 was developed when the ortho group is F, Cl, Br, and NO 2 on aromatic rings. Meanwhile, disulfides (diselenides) were also quickly constructed when the ortho group is H. These transformations undergo cascade thiophene construction/selective C3‐position thiolation process, featuring simple operations, divergent synthesis, broad substrate scope, readily available starting materials, and valuable products. A novel plausible radical annulation process was proposed and validated by DFT calculations for the first time. A series of derivatizations about the thiophene (TBT) and disulfides were also well‐represented.