电泳剂
化学选择性
化学
杂原子
组合化学
硫黄
戒指(化学)
有机化学
催化作用
作者
Dong‐Hang Tan,Zhihao Chen,Libin Yang,Changting Li,Fang-Hai Tu,Qingjiang Li,Honggen Wang
标识
DOI:10.1007/s11426-021-1188-x
摘要
The semipinacol rearrangement is one of the classic yet useful synthetic tools in organic synthesis. However, semipinacol rearrangements involving heteroatom-migration are rare. Reported herein is a boryl-migratory semipinacol rearrangement of α-hydroxyallylboronates and α-hydroxypropargylboronates triggered by diverse halogen-, oxygen-, sulfur- and selenium-containing electrophiles. The protocol leads to a mild and facile access to organoborons bearing valuable functionalities. The σ (C—B) hyperconjugation is believed to be the key factor that leads to the observed exclusive chemoselectivity and enhanced reactivity. Synthetic utilities of the formed products were demonstrated.
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