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α-氧代乙烯砜与烷基锌试剂的镍催化交叉偶联反应选择性合成烯醇醚

Selective synthesis of enol ethers nickel-catalyzed cross coupling of α-oxy-vinylsulfones with alkylzinc reagents.

机构信息

Department of Emergency, State Key Laboratory of Biotherapy, West China Hospital, and School of Chemical Engineering, Sichuan University, No. 17 Renmin Nan Road, Chengdu, 610041, China.

College of Pharmacy, Third Military Medical University, Gaotanyan Street, Shapingba District, Chongqing 400038, China.

出版信息

Chem Commun (Camb). 2021 Nov 19;57(92):12273-12276. doi: 10.1039/d1cc05347g.

DOI:10.1039/d1cc05347g
PMID:34734604
Abstract

We describe here a Ni-catalyzed Negishi coupling reaction to prepare 1,2-dialkyl enol ethers in a stereoconvergent fashion. This method employs readily available and bench-stable α-oxy-vinylsulfones as electrophiles. The C-sulfone bond in the α-oxy-vinylsulfone motif is cleaved chemoselectively in these reactions. The mild conditions are tolerant of a variety of functional groups on both partners, thus representing a general strategy for enol ether synthesis. This unique reactivity of α-oxy-vinylsulfones indicates their further application as electrophilic partners in cross-coupling reactions.

摘要

我们在这里描述了一种镍催化的 Negishi 偶联反应,以立体协同的方式制备 1,2-二烷基烯醇醚。该方法采用易得且稳定的α-氧代乙烯砜作为亲电试剂。在这些反应中,α-氧代乙烯砜结构中的 C-砜键被选择性地切断。温和的条件对两种反应物上的各种官能团都具有耐受性,因此代表了烯醇醚合成的一般策略。α-氧代乙烯砜的这种独特反应性表明它们可以进一步作为亲电试剂应用于交叉偶联反应中。

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