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

IF 4.6 1区化学 Q1 CHEMISTRY, ORGANIC Organic Chemistry Frontiers Pub Date : 2025-01-07 DOI:10.1039/d4qo02061h

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

引用次数: 0

Abstract

Ortho-alkylated phenols are widely exist innatural 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 serize of ortho-allylphenols. The C(sp³)-hydroxyl group was activated through intramolecular interaction 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 subsequent transformation into high-value scaffolds

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来源期刊

Organic Chemistry Frontiers CHEMISTRY, ORGANIC-

CiteScore

7.90

自引率

11.10%

发文量

686

审稿时长

1 months

期刊介绍： Organic Chemistry Frontiers is an esteemed journal that publishes high-quality research across the field of organic chemistry. It places a significant emphasis on studies that contribute substantially to the field by introducing new or significantly improved protocols and methodologies. The journal covers a wide array of topics which include, but are not limited to, organic synthesis, the development of synthetic methodologies, catalysis, natural products, functional organic materials, supramolecular and macromolecular chemistry, as well as physical and computational organic chemistry.