有機合成化学協会誌
Online ISSN : 1883-6526
Print ISSN : 0037-9980
ISSN-L : 0037-9980
総説および総合論文
銅触媒を用いる有機ボロン酸類の電子欠損性アルキンへの共役付加反応
山本 芳彦
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2013 年 71 巻 4 号 p. 296-306

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In the presence of catalytic amounts of copper salts, CuOAc or Cu(OAc)2, the reaction of arylboronic acids with electron-deficient alkynes proceeded in MeOH at ambient temperature to afford hydroarylation products with high chemo- and stereoselectivity. This method of synthesizing tri-substituted alkenes was further applied to the synthesis of biologically interesting molecules such as butenolides/pentenolides, 4-arylcoumarins, 3,3-diarylacrylonitriles, and 3-arylindole-2-carboxylates. Among them, the tandem hydroarylation/lactonization leading to 4-arylcoumarins is particularly fascinating as seven natural products were synthesized by the combination of three alkynoates and four boronic acids.
The copper-catalyzed conjugate addition was further extended to that of allylboronates as organoboron reagents. Thus, the copper-catalyzed conjugate allylation of various electron-deficient alkynes was achieved and the derivatization of the introduced allyl moiety was also investigated.

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