Synthesis of Multisubstituted Olefins through Regio- and Stereoselective Silylborylation of an Alkynylboronate/Chemoselective Cross-Coupling Sequences
Synthesis of Multisubstituted Olefins through Regio- and Stereoselective Silylborylation of an Alkynylboronate/Chemoselective Cross-Coupling Sequences
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DOI：
10.1021/ol401333j
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发表时间：
2013-07-05
期刊：
影响因子：
5.2
通讯作者：
Nishihara, Yasushi
中科院分区：
文献类型：
--
作者：
Jiao, Jiao;Nakajima, Kiyohiko;Nishihara, Yasushi
公开了炔基硼酸酯的高度区域选择性和立体选择性甲硅烷基化。 PhMe2Si-B-pin 经过 Pd(OAc)(2)/(t)OctNC 催化与炔基硼酸酯的顺加成反应，生成具有高区域选择性的 1-苯基-1-甲硅烷基-2,2-二硼基乙烯。然后通过Suzuki-Miyaura偶联将产物1-苯基-1-甲硅烷基-2,2-二硼基乙烯化学选择性芳基化，得到(2)-1-甲硅烷基-2-硼基芪衍生物。该方法扩展到具有四个不同取代基的四芳基化烯烃的合成。
A highly regio- and stereoselective silylborylation of an alkynylboronate is disclosed. PhMe2Si-B-pin undergoes a Pd(OAc)(2)/(t)OctNC-catalyzed syn-addition to the alkynylboronate to yield 1-phenyl-1-silyl-2,2-diborylethene with high regioselectivity. The product 1-phenyl-1-silyl-2,2-diborylethene is then chemoselectively arylated by Suzuki-Miyaura coupling to afford (2)-1-silyl-2-borylstilbene derivatives. This approach is extended to the synthesis of a tetraarylated olefin with four different substituents.