Stereoselective Cross-Coupling Reaction of 2,4-Diaryl-1,1-diboryl-1,3-butadienes: Stereocontrolled Approach to 1,3,4,6-Tetraarylated 1,3,5-Hexatrienes
作者:Masaki Shimizu、Katsuhiro Shimono、Michael Schelper、Tamejiro Hiyama
DOI:10.1055/s-2007-982567
日期:2007.7
The boryl group cis to the C(3)=C(4) group in 2,4-aryl-1,1-bis(pinacolatoboryl)-1,3-butadienes undergoes Pd-catalyzed cross-coupling reaction with aryl iodides stereoselectively at room temperature, giving rise to the corresponding boronates as a single diastereomer. Subsequent coupling of the boronates with alkenyl iodides allows us to synthesize 1,3,4,6-tetraarylated 1,3,5-hexatrienes stereoselectively.
在室温下,2,4-芳基-1,1-双(频哪醇氧羰基)-1,3-丁二烯中与 C(3)=C(4) 基顺式的硼烷基会在钯催化下与芳基碘化物立体选择性地发生交叉偶联反应,生成相应的硼酸盐单非对映异构体。随后,硼酸盐与烯基碘化物发生偶联反应,使我们能够立体选择性地合成 1,3,4,6-四芳基化的 1,3,5-己三烯。