• 文献检索
  • 文档翻译
  • 深度研究
  • 学术资讯
  • Suppr Zotero 插件Zotero 插件
  • 邀请有礼
  • 套餐&价格
  • 历史记录
应用&插件
Suppr Zotero 插件Zotero 插件浏览器插件Mac 客户端Windows 客户端微信小程序
定价
高级版会员购买积分包购买API积分包
服务
文献检索文档翻译深度研究API 文档MCP 服务
关于我们
关于 Suppr公司介绍联系我们用户协议隐私条款
关注我们

Suppr 超能文献

核心技术专利:CN118964589B侵权必究
粤ICP备2023148730 号-1Suppr @ 2026

文献检索

告别复杂PubMed语法,用中文像聊天一样搜索,搜遍4000万医学文献。AI智能推荐,让科研检索更轻松。

立即免费搜索

文件翻译

保留排版,准确专业,支持PDF/Word/PPT等文件格式,支持 12+语言互译。

免费翻译文档

深度研究

AI帮你快速写综述,25分钟生成高质量综述,智能提取关键信息,辅助科研写作。

立即免费体验

过渡金属催化的不对称硼氢化反应的最新进展。

Recent advances in asymmetric borylation by transition metal catalysis.

作者信息

Hu Jiefeng, Ferger Matthias, Shi Zhuangzhi, Marder Todd B

机构信息

Institute of Inorganic Chemistry, and Institute for Sustainable Chemistry & Catalysis with Boron, Julius-Maximilians-Universität Würzburg, Am Hubland, 97074 Würzburg, Germany.

Institute of Advanced Synthesis, School of Chemistry and Molecular Engineering, Nanjing Tech University, 211816 Nanjing, China.

出版信息

Chem Soc Rev. 2021 Nov 29;50(23):13129-13188. doi: 10.1039/d0cs00843e.

DOI:10.1039/d0cs00843e
PMID:34709239
Abstract

Chiral organoboronates have played a critical role in organic chemistry and in the development of materials science and pharmaceuticals. Much effort has been devoted to exploring synthetic methodologies for the preparation of these compounds during the past few decades. Among the known methods, asymmetric catalysis has emerged as a practical and highly efficient strategy for their straightforward preparation, and recent years have witnessed remarkable advances in this respect. Approaches such as asymmetric borylative addition, asymmetric allylic borylation and stereospecific cross-coupling borylation, have been extensively explored and well established employing transition-metal catalysis with a chiral ligand. This review provides a comprehensive overview of transition metal-catalysed asymmetric borylation processes to construct carbon-boron, carbon-carbon, and other carbon-heteroatom bonds. It summarises a range of recent achievements in this area of research, with considerable attention devoted to the reaction modes and the mechanisms involved.

摘要

手性有机硼酸酯在有机化学、材料科学和药物开发中发挥了关键作用。在过去几十年里,人们投入了大量精力探索这些化合物的合成方法。在已知方法中,不对称催化已成为直接制备它们的实用且高效的策略,近年来在这方面取得了显著进展。诸如不对称硼氢化加成、不对称烯丙基硼化和立体选择性交叉偶联硼化等方法,已通过使用手性配体的过渡金属催化得到广泛探索并得以确立。本综述全面概述了过渡金属催化的不对称硼化过程,以构建碳 - 硼键、碳 - 碳键和其他碳 - 杂原子键。它总结了该研究领域的一系列最新成果,并对反应模式和相关机制给予了相当关注。

相似文献

1
Recent advances in asymmetric borylation by transition metal catalysis.过渡金属催化的不对称硼氢化反应的最新进展。
Chem Soc Rev. 2021 Nov 29;50(23):13129-13188. doi: 10.1039/d0cs00843e.
2
Asymmetric C(sp)-H borylation: an update.不对称 C(sp^2)-H 硼化反应:最新进展。
Org Biomol Chem. 2022 Jun 8;20(22):4496-4511. doi: 10.1039/d2ob00688j.
3
Development of Chiral Ligands for the Transition-Metal-Catalyzed Enantioselective Silylation and Borylation of C-H Bonds.发展过渡金属催化的 C-H 键手性硅化和硼化反应中的手性配体。
Angew Chem Int Ed Engl. 2022 Feb 21;61(9):e202113343. doi: 10.1002/anie.202113343. Epub 2021 Dec 21.
4
Boron-Heteroatom Addition Reactions via Borylative Heterocyclization: Oxyboration, Aminoboration, and Thioboration.硼杂原子加成反应通过硼化杂环化反应:氧硼化、胺硼化和硫硼化。
Acc Chem Res. 2017 Oct 17;50(10):2598-2609. doi: 10.1021/acs.accounts.7b00365. Epub 2017 Sep 21.
5
Transition metal-catalyzed efficient and green transformations of P(O)-H compounds to functional organophosphorus compounds.过渡金属催化的 P(O)-H 化合物高效、绿色转化为功能有机磷化合物。
Mini Rev Med Chem. 2013 May 1;13(6):824-35. doi: 10.2174/1389557511313060005.
6
Enantioselective Borylation of Aromatic C-H Bonds with Chiral Dinitrogen Ligands.手性双氮配体对芳环 C-H 键的对映选择性硼化反应。
Angew Chem Int Ed Engl. 2017 Jun 12;56(25):7205-7208. doi: 10.1002/anie.201702628. Epub 2017 May 16.
7
Enantioselective preparation and chemoselective cross-coupling of 1,1-diboron compounds.手性 1,1-二硼化合物的对映选择性制备和化学选择性交叉偶联。
Nat Chem. 2011 Sep 25;3(11):894-9. doi: 10.1038/nchem.1150.
8
Advances in Chiral Pincer Complexes: Insights and Applications in Catalytic Asymmetric Reactions.手性钳状配合物的研究进展:在催化不对称反应中的应用与展望。
Int J Mol Sci. 2024 Sep 26;25(19):10344. doi: 10.3390/ijms251910344.
9
Metal-catalysed C-H bond activation and borylation.金属催化的 C-H 键活化和硼化反应。
Chem Soc Rev. 2022 Jun 20;51(12):5042-5100. doi: 10.1039/d1cs01012c.
10
P-Chiral Phosphorus Ligands Based on a 2,3-Dihydrobenzo[ d][1,3]oxaphosphole Motif for Asymmetric Catalysis.基于 2,3-二氢苯并[ d][1,3]氧杂磷杂环戊烯骨架的手性磷配体在不对称催化中的应用。
Acc Chem Res. 2019 Apr 16;52(4):1101-1112. doi: 10.1021/acs.accounts.9b00029. Epub 2019 Mar 8.

引用本文的文献

1
Enantioselective synthesis of chiral 2,3-cis-disubstituted piperidines and C1-substituted tetrahydroisoquinolines by asymmetric Cu-catalyzed cyclizative aminoboration.通过不对称铜催化的环化氨基硼化反应对映选择性合成手性2,3-顺式二取代哌啶和C1-取代四氢异喹啉。
Nat Commun. 2025 Jul 25;16(1):6851. doi: 10.1038/s41467-025-61736-8.
2
Nickel-catalyzed diastereoselective hydroboration of acrylates with a vinylborane reagent.镍催化丙烯酸酯与乙烯基硼烷试剂的非对映选择性硼氢化反应。
Chem Sci. 2025 Jun 13. doi: 10.1039/d5sc02695d.
3
Palladium-catalyzed cross-coupling of -difluorocyclopropanes with -diborylalkanes: facile synthesis of a diverse array of -diboryl-substituted fluorinated alkenes.
钯催化的二氟环丙烷与二硼基烷烃的交叉偶联反应:多种二硼基取代的氟化烯烃的简便合成方法
RSC Adv. 2025 Apr 9;15(13):10265-10272. doi: 10.1039/d5ra00581g. eCollection 2025 Mar 28.
4
F NMR-Based Chiral Analysis of Organoboron Compounds via Chiral Recognition of Fluorine-Labeled Boronates with Cobalt Complexes.基于氟核磁共振的有机硼化合物手性分析:通过钴配合物对手性氟代硼酸酯的手性识别
JACS Au. 2024 Sep 16;4(10):3771-3776. doi: 10.1021/jacsau.4c00703. eCollection 2024 Oct 28.
5
The current utility and future potential of multiborylated alkanes.多硼化烷烃的当前用途及未来潜力。
Nat Rev Chem. 2024 Oct;8(10):741-761. doi: 10.1038/s41570-024-00650-x. Epub 2024 Sep 26.
6
Organocatalytic Asymmetric Allylic Benzylborylation via Fluoride-Assisted Catalytic Generation of α-Boryl Carbanionic Intermediates.通过氟化物辅助催化生成α-硼基碳负离子中间体的有机催化不对称烯丙基苄基硼化反应
Org Lett. 2024 Oct 4;26(39):8394-8399. doi: 10.1021/acs.orglett.4c03242. Epub 2024 Sep 20.
7
Asymmetric dihydroboration of allenes enabled by ligand relay catalysis.通过配体接力催化实现的丙二烯不对称二硼氢化反应。
Nat Commun. 2024 Sep 18;15(1):8186. doi: 10.1038/s41467-024-51774-z.
8
Stereospecific Phosphination and Thioetherification of Organoboronic Esters.有机硼酸酯的立体选择性膦化和硫醚化反应
J Am Chem Soc. 2024 Jul 17;146(28):18873-18878. doi: 10.1021/jacs.4c06526. Epub 2024 Jul 2.
9
Simultaneous Stereoinvertive and Stereoselective C(sp)-C(sp) Cross-Coupling of Boronic Esters and Allylic Carbonates.硼酸酯与烯丙基碳酸酯的同时立体反转和立体选择性C(sp)-C(sp)交叉偶联
J Am Chem Soc. 2024 May 22;146(20):13719-13726. doi: 10.1021/jacs.4c03686. Epub 2024 May 9.
10
One pot conversion of phenols and anilines to aldehydes and ketones exploiting α gem boryl carbanions.利用α-偕二硼基碳负离子一锅法将酚类和苯胺类化合物转化为醛类和酮类化合物。
Nat Commun. 2024 May 7;15(1):3794. doi: 10.1038/s41467-024-47156-0.