Palladium-catalyzed cycloisomerization of thiocarbamates with consecutive formation of quaternary carbon and sulfide

被引：0
|
作者：
Kumazawa, Hyu [1 ]
Nakada, Masahisa [1 ]
机构：
[1] Waseda Univ, Sch Adv Sci & Engn, Dept Chem & Biochem, 3-4-1 Ohkubo,Shinjuku Ku, Tokyo 1698555, Japan
来源：
TETRAHEDRON LETTERS | 2025年 / 154卷
关键词：
Bridged-ring; Cycloisomerization; Palladium; Quaternary carbon; Sulfide; Thiocarbamate; ALKALOIDS; THIOESTERS; AMIDATION; ALKENES;
D O I：
10.1016/j.tetlet.2024.155384
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The Pd-catalyzed cycloisomerization of thiocarbamates with consecutive formation of a quaternary carbon and a sulfide is described. This Pd-catalyzed cascade reaction occurred with both alkylthiocarbamates and arylthiocarbamates, and arylthiocarbamates reacted faster than alkylthiocarbamates. The Pd-catalyzed cycloisomerization can be applied to phenylene- and alkylene-tethered substrates, and thiocarbamate was found to be less reactive than carbamimidothioate. The Pd-catalyzed cycloisomerization can be used to form bridged rings and is expected to be useful for ring construction of nitrogen-containing polycyclic natural products.
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页数：7
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