4.7 Article

A boryl-migratory semipinacol rearrangement

Journal

SCIENCE CHINA-CHEMISTRY
Volume 65, Issue 4, Pages 746-752

Publisher

SCIENCE PRESS
DOI: 10.1007/s11426-021-1188-x

Keywords

1; 2-boryl migration; hyperconjugation; iterative cross-coupling; organoborons; semipinacol rearrangement; sp(3)-B; tetra-substituted alkene

Funding

  1. National Natural Science Foundation of China [22022114, 21971261]
  2. Key Project of Chinese National Programs for Fundamental Research and Development [2016YFA0602900]
  3. Guang-dong Basic and Applied Basic Research Foundation [2020A1515010624]
  4. Fundamental Research Funds for the Central Universities [20ykzd12]
  5. Local Innovative and Research Teams Project of Guangdong Pearl River Talents Program [2017BT01Y093]
  6. China Postdoctoral Science Foundation [2021M69360]

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A boryl-migratory semipinacol rearrangement of alpha-hydroxyallylboronates and alpha-hydroxypropargylboronates triggered by diverse halogen-, oxygen-, sulfur- and selenium-containing electrophiles was reported in this study. The method provides a mild and facile access to organoborons bearing valuable functionalities, with the sigma (C-B) hyperconjugation believed to be the key factor leading to the observed exclusive chemoselectivity and enhanced reactivity. The synthetic utilities of the formed products were demonstrated.
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 alpha-hydroxyallylboronates and alpha-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 sigma (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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