Construction of 1,3-Diboryl Allenes from gem-Iododiboron Compounds via Intermolecular Boryl Group Transfer
Ming Li , Yi Wei , Du Chen , Peng-Fei Ning , Yi-Fei Yang , Xiao-Yu Xie , Chao Liu , Kai Hong
Chinese Journal of Chemistry ›› 2025, Vol. 43 ›› Issue (8) : 949 -955.
Construction of 1,3-Diboryl Allenes from gem-Iododiboron Compounds via Intermolecular Boryl Group Transfer
Allenylboronates are valuable synthetic building blocks and have garnered significant interest. However, their 1,3-diboyl substituted analogs have not been reported. Herein, we disclosed a novel method for creating 1,3-diboyl allenes from gem-iododiboron compounds and alkynyl Grignard reagents. The starting materials are initially converted into the corresponding propargylic gem-bis(boronates), which then undergo an intermolecular boryl group transfer to afford 1,3-diboyl allenes, as confirmed by mechanistic studies. This method features good tolerance to steric hindrance and is compatible with a wide variety of functional groups.
Allenes / Organoboron / Iododiboron / Grignard reagents / Isomerization / Migration / Organohalides / Isotopes / Nucleophilic substitution / Synthetic methods
2025 SIOC, CAS, Shanghai, & WILEY-VCH GmbH.
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