Effective synthesis of aryl ethers and coumaranones employing the palladium-catalyzed enyne-diyne [4+2] cycloaddition protocol

被引:26
作者
Gevorgyan, V [1 ]
Quan, LG [1 ]
Yamamoto, Y [1 ]
机构
[1] Tohoku Univ, Grad Sch Sci, Dept Chem, Sendai, Miyagi 98077, Japan
关键词
D O I
10.1021/jo991519k
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Alkyl-, alkoxy-, and aryloxy-substituted conjugated enynes 1 in the presence of Pd(PPh3)(4) catalyst smoothly underwent the regiospecific [4 + 2] cycloaddition reaction with conjugated alkyl- and alkoxy-substituted symmetric diynes 2 to give multisubstituted aryl ethers 3 in good to high yields. Benzannulation of enynes 1d-g with unsymmetric diyne 6, possessing alkyl and alkoxy groups at acetylenic terminii, in most cases produced an aromatic product 8 with an alkoxy group of diyne attached to the ethynyl moiety of the aromatic product. Remarkably, alkoxy-substituted diynes 2c and 6 underwent the benzannulation reaction with 1 at an unusually low temperature of 0 degrees C! One-pot consecutive benzannulation of alkyl-substituted enynes 1d,e and alkoxy-substituted enynes 1f,g with alkoxy-substituted diynes 2c and 6 followed by protonolysis with TsOH afforded coumaranones 9a-c and 10 in reasonable to high overall yields.
引用
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页码:568 / 572
页数:5
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