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Highly Efficient Synthesis of Allenes from Trimethylaluminum Reagent and Propargyl Acetates Mediated by a Palladium Catalyst
Author(s) -
Li QingHan,
Jeng JungYuan,
Gau HanMou
Publication year - 2014
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.201403008
Subject(s) - chemistry , propargyl , allene , palladium , catalysis , reagent , phosphine , electrophile , organic chemistry , tetrahydrofuran , combinatorial chemistry , solvent
A series of propargyl acetates were prepared and used as propargyl electrophiles for coupling reactions with trimethylaluminum. The simple catalytic system of palladium(II) acetate (1 mol‐%) and tri( o ‐tolyl)phosphine (2 mol‐%) worked efficiently for a wide variety of aromatic and aliphatic propargyl acetates, producing the substituted allenes in good to excellent yields of up to 94 % in tetrahydrofuran. The process was simple and easily performed, and it provides an efficient method for the synthesis of substituted allene derivatives. On the basis of the experimental results, a possible catalytic cycle has been proposed.