通过碳氮键和碳氧键活化实现的镍催化、立体专一性碳-碳和碳-硼交叉偶联反应。
Nickel-Catalyzed, Stereospecific C-C and C-B Cross-Couplings via C-N and C-O Bond Activation.
作者信息
Xu Jianyu, Bercher Olivia P, Talley Michael R, Watson Mary P
机构信息
Department of Chemistry & Biochemistry, University of Delaware, Newark, Delaware 19716, United States.
出版信息
ACS Catal. 2021 Feb 5;11(3):1604-1612. doi: 10.1021/acscatal.0c05484. Epub 2021 Jan 19.
Abstract
Highly enantioenriched benzylic and allylic amines and alcohols are readily available via asymmetric synthesis and in complex natural products. The development of mild, nickel-catalyzed cross-couplings of their derivatives has advanced the tools available for the preparation of a range of highly enantioenriched products, including those with quaternary stereocenters. This perspective focuses on cross-couplings with convenient and functional group-tolerant organoboron reagents and highlights the discoveries of activating groups and conditions that have led to high-yielding and highly stereospecific reactions. Emphasis is placed on mechanistic understanding, particularly with regards to controlling inversion vs. retention pathways. Limitations and opportunities for future developments are also highlighted.
摘要
通过不对称合成以及复杂天然产物中，可轻松获得高对映体富集的苄基和烯丙基胺及醇。其衍生物温和的镍催化交叉偶联反应的发展，推进了一系列高对映体富集产物制备工具的发展，包括那些具有季立体中心的产物。本综述着重于与方便且官能团耐受性好的有机硼试剂的交叉偶联反应，并突出了导致高产率和高立体专一性反应的活化基团及条件的发现。重点在于机理理解，特别是关于控制构型翻转与构型保持途径方面。同时也强调了未来发展的局限性和机遇。
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