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Palladium‐Catalyzed Coupling of Propargylic Carbonates with N ‐Tosylhydrazones: Highly Selective Synthesis of Substituted Propargylic N ‐Sulfonylhydrazones and Vinylallenes
Author(s) -
Chen ZiSheng,
Duan XinHua,
Wu LuYong,
Ali Shaukat,
Ji KeGong,
Zhou PingXin,
Liu XueYuan,
Liang YongMin
Publication year - 2011
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201100248
Subject(s) - palladium , catalysis , propane , chemistry , coupling (piping) , medicinal chemistry , organic chemistry , materials science , metallurgy
An efficient palladium‐catalyzed coupling of propargylic carbonates ( 1 ) with N ‐tosylhydrazones ( 2, 2′ ) has been carried out. A wide range of propargylic N ‐sulfonylhydrazones ( 3 ) and multisubstituted vinylallenes ( 4 ) can be obtained selectively by using either [PdCl 2 (CH 3 CN) 2 ] or [Pd 2 (dba) 3 ] as catalysts. (dba= trans , trans ‐dibenzylideneacetone, dppp=propane‐l,3‐diylbis(diphenylphosphane), Ts=4‐toluenesulfonyl.)