Transition-metal-free C(sp3)-C(sp2) couplings with secondary alcohols and boronic acids via neighboring group activation

Xingxing Yang, Yourong Pan, Cheng Ren, Chengrui Hu, Feng Wan, Hongliang Duan, Chengxi Li

Research output: Contribution to journalArticlepeer-review

Abstract

Ortho-Alkylated phenols are widely found in natural products and bioactive compounds. Here we have developed a mild, transition-metal-free approach for the C(sp3)-C(sp2) cross-coupling of alkenyl boronic acids with secondary alcohols via neighboring group activation, furnishing a series of ortho-allylphenols. The C(sp3)-hydroxyl group was activated through intramolecular interactions with ortho-phenolic functional groups (triflyl, tert-butoxycarbonyl, phosphoryl, and cyclic carbonate). This method exhibits good substrate compatibility, allowing for the efficient synthesis of ortho-allyl phenols and their subsequent transformation into high-value scaffolds.

Original languageEnglish
JournalOrganic Chemistry Frontiers
DOIs
Publication statusAccepted/In press - 2025

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