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铜催化的C(sp)-Si和C(sp)-B键形成的最新进展。

Recent advances in Cu-catalyzed C(sp)-Si and C(sp)-B bond formation.

作者信息

Takale Balaram S, Thakore Ruchita R, Etemadi-Davan Elham, Lipshutz Bruce H

机构信息

Department of Chemistry & Biochemistry, University of California, Santa Barbara, California 93106, USA.

出版信息

Beilstein J Org Chem. 2020 Apr 15;16:691-737. doi: 10.3762/bjoc.16.67. eCollection 2020.

DOI:10.3762/bjoc.16.67
PMID:32362947
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC7176932/
Abstract

Numerous reactions generating C-Si and C-B bonds are in focus owing to the importance of incorporating silicon or boron into new or existing drugs, in addition to their use as building blocks in cross-coupling reactions en route to various targets of both natural and unnatural origins. In this review, recent protocols relying on copper-catalyzed sp carbon-silicon and carbon-boron bond-forming reactions are discussed.

摘要

由于将硅或硼纳入新的或现有的药物中具有重要意义，以及它们在通向各种天然和非天然来源目标的交叉偶联反应中作为构建单元的用途，众多生成碳 - 硅键和碳 - 硼键的反应受到关注。在本综述中，将讨论依赖铜催化的sp碳 - 硅和碳 - 硼键形成反应的最新方法。

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5
Beyond Carbon: Enantioselective and Enantiospecific Reactions with Catalytically Generated Boryl- and Silylcopper Intermediates.超越碳：利用催化生成的硼基和硅基铜中间体进行的对映选择性和对映体特异性反应
ACS Cent Sci. 2020 Jul 22;6(7):1070-1081. doi: 10.1021/acscentsci.0c00738. Epub 2020 Jul 9.
Catalytic Enantioselective Synthesis of Allylic Boronates Bearing a Trisubstituted Alkenyl Fluoride and Related Derivatives.
手性催化 allylic 硼酸盐的三取代烯基氟化物及相关衍生物的合成。
Angew Chem Int Ed Engl. 2019 Aug 26;58(35):11998-12003. doi: 10.1002/anie.201906283. Epub 2019 Jul 16.
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Copper-catalyzed regiodivergent 1,4- and 1,6-conjugate silyl addition to diendioates: access to functionalized allylsilanes.铜催化的区域发散 1,4-和 1,6-共轭硅基加成到二烯二酸酯：官能化烯丙基硅烷的获得。
Org Biomol Chem. 2019 Jun 26;17(25):6122-6126. doi: 10.1039/c9ob01086f.
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Copper(I)-Catalyzed Enantioconvergent Borylation of Racemic Benzyl Chlorides Enabled by Quadrant-by-Quadrant Structure Modification of Chiral Bisphosphine Ligands.铜（I）催化的外消旋苄基氯化物的对映转化硼化反应，通过手性双膦配体的象限-象限结构修饰来实现。
Angew Chem Int Ed Engl. 2019 Aug 5;58(32):11112-11117. doi: 10.1002/anie.201906011. Epub 2019 Jul 3.
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Copper-Catalyzed Regio- and Enantioselective Addition of Silicon Grignard Reagents to Alkenes Activated by Azaaryl Groups.铜催化硅基格氏试剂对氮杂芳基活化烯烃的区域和对映选择性加成反应
Angew Chem Int Ed Engl. 2019 Jul 29;58(31):10723-10726. doi: 10.1002/anie.201905934. Epub 2019 Jun 24.
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The Mechanism of Copper-Catalyzed Trifunctionalization of Terminal Allenes.铜催化末端联烯的三官能团化反应机理
Chemistry. 2019 Jul 17;25(40):9456-9463. doi: 10.1002/chem.201900673. Epub 2019 Apr 30.
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meta-Selective C-H Borylation of Benzamides and Pyridines by an Iridium-Lewis Acid Bifunctional Catalyst.铱-路易斯酸双功能催化剂实现苯甲酰胺和吡啶的间位选择性 C-H 硼化反应。
J Am Chem Soc. 2019 May 15;141(19):7972-7979. doi: 10.1021/jacs.9b03138. Epub 2019 May 1.
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Tertiary α-Silyl Alcohols by Diastereoselective Coupling of 1,3-Dienes and Acylsilanes Initiated by Enantioselective Copper-Catalyzed Borylation.通过对映选择性铜催化硼氢化反应引发的1,3-二烯与酰基硅烷的非对映选择性偶联制备叔α-硅基醇。
Angew Chem Int Ed Engl. 2019 Jun 11;58(24):8211-8215. doi: 10.1002/anie.201903174. Epub 2019 May 15.
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Regiodivergent and Stereospecific Aziridine Opening by Copper-Catalyzed Addition of Silicon Grignard Reagents.铜催化硅基格氏试剂加成实现区域发散性和立体特异性的氮丙啶开环反应
Chemistry. 2019 May 7;25(26):6505-6507. doi: 10.1002/chem.201901128. Epub 2019 Apr 16.