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Palladium‐Catalyzed Desulfurative Carbocyclizations of α‐(3‐Butenoyl) Ketene Dithioacetals in the Presence of Silanes
Author(s) -
Liu Bangyu,
Chang Jian,
Zheng Gang,
Song Xiaoning,
Wang Mang
Publication year - 2015
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201500453
Subject(s) - ketene , silanes , chemistry , palladium , silane , catalysis , triphenylphosphine , bond cleavage , medicinal chemistry , dimethylformamide , organic chemistry , polymer chemistry , solvent
A combination of palladium and silane has been well used for the catalytic desulfurative cross‐coupling reactions under neutral conditions. Catalyzed by 10 mol‐% of bis(triphenylphosphine) palladium(II) dichloride in dimethylformamide in the presence of 2 equiv. of triphenylsilane, the carbocyclizations of α‐(3‐butenoyl) ketene dithioacetals took place smoothly leading to 2‐cyclopentenones in high yields. Thus, a new Heck‐type cyclization based on C–S bond cleavage for the synthesis of spiro compounds by using silanes as the desulfurative agents has been established.