Rhodium- and iridium-catalyzed oxidative coupling of benzoic acids with alkynes via regioselective C-H bond cleavage

被引:472
作者
Ueura, Kenji [1 ]
Satoh, Tetsuya [1 ]
Miura, Masahiro [1 ]
机构
[1] Osaka Univ, Fac Engn, Dept Appl Chem, Suita, Osaka 5650871, Japan
关键词
D O I
10.1021/jo070735n
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The oxidative coupling of benzoic acids with internal alkynes effectively proceeds in the presence of [Cp*RhCl2](2) and Cu(OAc)(2)center dot H2O as catalyst and oxidant, respectively, to produce the corresponding isocoumarin derivatives. The copper salt can be reduced to a catalytic quantity under air. Interestingly, by using [Cp*IrCl2](2) in place of [Cp*RhCl2](2), the substrates undergo 1:2 coupling accompanied by decarboxylation to afford naphthalene derivatives exclusively. In this case, Ag2CO3 acts as an effective oxidant.
引用
收藏
页码:5362 / 5367
页数:6
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