• 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

卤硼化反应：范围、机理及应用

Haloboration: scope, mechanism and utility.

作者信息

Kirschner Sven, Yuan Kang, Ingleson Michael J

机构信息

EaStCHEM School of Chemistry, University of Edinburgh Edinburgh EH9 3FJ UK

出版信息

New J Chem. 2020 Jul 8;45(33):14855-14868. doi: 10.1039/d0nj02908d. eCollection 2021 Aug 23.

DOI:10.1039/d0nj02908d
PMID:34483652
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC8381870/
Abstract

Haloboration, the addition of B-X (X = Cl, Br, I) across an unsaturated moiety , C[double bond, length as m-dash]Y or C[triple bond, length as m-dash]Y (Y = C, N, ), is dramatically less utilised than the ubiquitous hydroboration reaction. However, haloboration of alkynes in particular is a useful tool to access ambiphilic 1,2-disubstituted alkenes. The stereochemical outcome of the reaction is easily controlled and the resulting products have proven to be valuable building blocks in organic synthesis and materials chemistry. This review aims at providing the reader with a brief summary of the historic development and of the current mechanistic understanding of this transformation. Recent developments are discussed and select examples demonstrating the use of haloboration products are given with a focus on the major areas, specifically, natural product synthesis and the development of boron-doped polycyclic aromatic hydrocarbons (B-PAHs).

摘要

卤硼化反应是指B-X（X = Cl、Br、I）加成到不饱和部分C=C或C≡C（Y = C、N等）上的反应，与无处不在的硼氢化反应相比，其应用要少得多。然而，尤其是炔烃的卤硼化反应是制备双亲性1,2-二取代烯烃的有用工具。该反应的立体化学结果易于控制，并且所得产物已被证明是有机合成和材料化学中有价值的构建单元。本综述旨在为读者简要总结该转化反应的历史发展以及当前的机理认识。讨论了近期的进展，并给出了一些展示卤硼化产物用途的精选实例，重点关注主要领域，特别是天然产物合成和硼掺杂多环芳烃（B-PAHs）的开发。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2b47/8381870/434c5cb7b6fa/d0nj02908d-p3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2b47/8381870/0584d31887f5/d0nj02908d-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2b47/8381870/16e791814d67/d0nj02908d-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2b47/8381870/4253affe7c2a/d0nj02908d-s3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2b47/8381870/97d5698b6088/d0nj02908d-s4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2b47/8381870/6ab2d60138ff/d0nj02908d-s5.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2b47/8381870/033ae5fde75b/d0nj02908d-s6.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2b47/8381870/9cb93272078f/d0nj02908d-s7.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2b47/8381870/ca61d2f47694/d0nj02908d-s8.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2b47/8381870/5188c7478140/d0nj02908d-s9.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2b47/8381870/a089234932f0/d0nj02908d-s10.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2b47/8381870/66b9541cab8c/d0nj02908d-s11.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2b47/8381870/460677f4893b/d0nj02908d-s12.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2b47/8381870/f128c052b914/d0nj02908d-s13.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2b47/8381870/54418d3b4b40/d0nj02908d-s14.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2b47/8381870/6d9b54e88dea/d0nj02908d-s15.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2b47/8381870/ecfa398feb00/d0nj02908d-s16.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2b47/8381870/a14b8c14cc6d/d0nj02908d-s17.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2b47/8381870/a598357fd2e2/d0nj02908d-s18.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2b47/8381870/f39657823d04/d0nj02908d-s19.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2b47/8381870/4581393b0d4b/d0nj02908d-s20.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2b47/8381870/b02edff799aa/d0nj02908d-s21.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2b47/8381870/c9004a028155/d0nj02908d-s26.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2b47/8381870/c1d2a8252fdc/d0nj02908d-s27.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2b47/8381870/e466d072a2b2/d0nj02908d-p1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2b47/8381870/85e6baca0cc8/d0nj02908d-p2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2b47/8381870/434c5cb7b6fa/d0nj02908d-p3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2b47/8381870/0584d31887f5/d0nj02908d-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2b47/8381870/16e791814d67/d0nj02908d-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2b47/8381870/4253affe7c2a/d0nj02908d-s3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2b47/8381870/97d5698b6088/d0nj02908d-s4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2b47/8381870/6ab2d60138ff/d0nj02908d-s5.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2b47/8381870/033ae5fde75b/d0nj02908d-s6.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2b47/8381870/9cb93272078f/d0nj02908d-s7.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2b47/8381870/ca61d2f47694/d0nj02908d-s8.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2b47/8381870/5188c7478140/d0nj02908d-s9.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2b47/8381870/a089234932f0/d0nj02908d-s10.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2b47/8381870/66b9541cab8c/d0nj02908d-s11.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2b47/8381870/460677f4893b/d0nj02908d-s12.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2b47/8381870/f128c052b914/d0nj02908d-s13.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2b47/8381870/54418d3b4b40/d0nj02908d-s14.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2b47/8381870/6d9b54e88dea/d0nj02908d-s15.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2b47/8381870/ecfa398feb00/d0nj02908d-s16.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2b47/8381870/a14b8c14cc6d/d0nj02908d-s17.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2b47/8381870/a598357fd2e2/d0nj02908d-s18.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2b47/8381870/f39657823d04/d0nj02908d-s19.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2b47/8381870/4581393b0d4b/d0nj02908d-s20.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2b47/8381870/b02edff799aa/d0nj02908d-s21.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2b47/8381870/c9004a028155/d0nj02908d-s26.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2b47/8381870/c1d2a8252fdc/d0nj02908d-s27.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2b47/8381870/e466d072a2b2/d0nj02908d-p1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2b47/8381870/85e6baca0cc8/d0nj02908d-p2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2b47/8381870/434c5cb7b6fa/d0nj02908d-p3.jpg

相似文献

1
Haloboration: scope, mechanism and utility.卤硼化反应：范围、机理及应用
New J Chem. 2020 Jul 8;45(33):14855-14868. doi: 10.1039/d0nj02908d. eCollection 2021 Aug 23.
2
Fragmentation of oxygen-containing molecules via C-O bond cleavage promoted by coordination to niobium and tantalum pentahalides.通过与五卤化铌和钽配位促进的C-O键断裂实现含氧化合物分子的碎片化。
Dalton Trans. 2009 Sep 14(34):6759-72. doi: 10.1039/b905023j. Epub 2009 Jul 20.
3
One tool to bring them all: Au-catalyzed synthesis of B,O- and B,N-doped PAHs from boronic and borinic acids.将它们一网打尽的一种工具：通过硼酸和次硼酸实现金催化合成硼、氧和硼、氮掺杂的多环芳烃。
Chem Sci. 2021 Mar 17;12(16):5898-5909. doi: 10.1039/d1sc00543j.
4
Site-Fixed Hydroboration of Terminal and Internal Alkenes using BX / Pr NEt*.使用BX / Pr NEt*对末端和内烯烃进行位点固定硼氢化反应
Angew Chem Int Ed Engl. 2021 Dec 6;60(50):26238-26245. doi: 10.1002/anie.202111978. Epub 2021 Nov 5.
5
Mechanistic Insight from Lewis-Acid-Dependent Selectivity and Reversible Haloboration, as Harnessed for Boron-Based Electrophilic Cyclization Reactions.基于路易斯酸依赖性选择性和可逆卤硼化反应的机理洞察，用于硼基亲电环化反应。
J Org Chem. 2023 Nov 3;88(21):15159-15167. doi: 10.1021/acs.joc.3c01653. Epub 2023 Oct 25.
6
Haloboration of o-Alkynyl Phenols Generates Halogenated Bicyclic-Boronates.邻炔基苯酚的硼氢化反应生成卤代双环硼酸酯。
Angew Chem Int Ed Engl. 2023 Apr 17;62(17):e202301463. doi: 10.1002/anie.202301463. Epub 2023 Mar 20.
7
Haloboration of internal alkynes with boronium and borenium cations as a route to tetrasubstituted alkenes.内炔烃与鏻和硼阳离子的卤化硼反应是合成四取代烯烃的一种途径。
Angew Chem Int Ed Engl. 2013 Jul 15;52(29):7518-22. doi: 10.1002/anie.201302609. Epub 2013 Jun 5.
8
Synthesis, structure, and reactivity of iridium perfluorocarbene complexes: regio- and stereo-specific addition of HCl across a metal carbon double bond.铱全氟卡宾配合物的合成、结构与反应活性：HCl跨金属碳双键的区域和立体特异性加成
Dalton Trans. 2015 Dec 7;44(45):19528-42. doi: 10.1039/c5dt02275d. Epub 2015 Jul 27.
9
The synthesis of brominated-boron-doped PAHs by alkyne 1,1-bromoboration: mechanistic and functionalisation studies.通过炔烃1,1-溴硼化反应合成溴代硼掺杂多环芳烃：机理与官能团化研究
Chem Sci. 2020 Feb 27;11(12):3258-3267. doi: 10.1039/c9sc05404a.
10
The d4/d3 redox pairs [MX(CO)(eta-RC[triple bond, length as m-dash]CR)Tp']z (z=0 and 1): structural consequences of electron transfer and implications for the inverse halide order.d4/d3氧化还原对[MX(CO)(η-RC≡CR)Tp']z（z = 0和1）：电子转移的结构后果及对反常卤化物顺序的影响
Dalton Trans. 2007 Jan 7(1):62-72. doi: 10.1039/b611472e. Epub 2006 Oct 31.

引用本文的文献

1
Diversity-oriented synthesis of stereodefined tetrasubstituted alkenes via a modular alkyne gem-addition strategy.通过模块化炔烃偕加成策略实现立体定向四取代烯烃的多样性导向合成。
Nat Commun. 2025 Jan 25;16(1):1025. doi: 10.1038/s41467-025-56184-3.
2
Transition-Metal-Free Thioboration of Terminal Alkynes.末端炔烃的无过渡金属硫硼化反应
JACS Au. 2024 Nov 15;4(12):4927-4933. doi: 10.1021/jacsau.4c00907. eCollection 2024 Dec 23.
3
A practical preparation of bicyclic boronates via metal-free heteroatom-directed alkenyl sp-C‒H borylation.

本文引用的文献

1
The synthesis of brominated-boron-doped PAHs by alkyne 1,1-bromoboration: mechanistic and functionalisation studies.通过炔烃1,1-溴硼化反应合成溴代硼掺杂多环芳烃：机理与官能团化研究
Chem Sci. 2020 Feb 27;11(12):3258-3267. doi: 10.1039/c9sc05404a.
2
Intramolecular (directed) electrophilic C-H borylation.分子内（定向）亲电碳-氢键硼化反应。
Chem Soc Rev. 2020 Jun 4. doi: 10.1039/c9cs00763f.
3
Stereoselective Bromoboration of Acetylene with Boron Tribromide: Preparation and Cross-Coupling Reactions of ()-Bromovinylboronates.三溴化硼对乙炔的立体选择性溴化：（）-溴乙烯基硼酸酯的制备和交叉偶联反应。
通过无金属杂原子导向的烯基sp-C-H硼化反应制备双环硼酸酯的实用方法。
Commun Chem. 2023 Aug 23;6(1):176. doi: 10.1038/s42004-023-00976-5.
4
Mechanistic Analysis of Alkyne Haloboration: A DFT, MP2, and DLPNO-CCSD(T) Study.炔烃卤硼化反应的机理分析：一项DFT、MP2和DLPNO-CCSD(T)研究。
J Phys Chem A. 2023 Aug 3;127(30):6135-6146. doi: 10.1021/acs.jpca.3c00607. Epub 2023 Jul 25.
5
Two Directing Groups Used for Metal Catalysed -C-H Functionalisation Only Effect Electrophilic C-H Borylation.仅用于金属催化的-C-H官能化的两个导向基团仅影响亲电C-H硼化反应。
European J Org Chem. 2022 Nov 25;2022(44):e202200901. doi: 10.1002/ejoc.202200901.
6
Free Radical Isomerizations in Acetylene Bromoboration Reaction.乙炔溴化反应中的自由基异构化。
Molecules. 2021 Apr 25;26(9):2501. doi: 10.3390/molecules26092501.
J Org Chem. 2020 Jun 5;85(11):6992-7000. doi: 10.1021/acs.joc.0c00341. Epub 2020 May 21.
4
Access to Stereodefined ()-2-Silylallylboronates via Regioselective Chloroboration of Allenylsilanes.通过烯丙基硅烷的区域选择性氯硼化反应获得立体定向的()-2-硅基烯丙基硼酸酯。
Org Lett. 2019 Dec 6;21(23):9541-9544. doi: 10.1021/acs.orglett.9b03720. Epub 2019 Nov 12.
5
BN-Embedded Tetrabenzopentacene: A Pentacene Derivative with Improved Stability.硼氮嵌入的四苯并戊省：一种稳定性得到改善的并五苯衍生物。
Angew Chem Int Ed Engl. 2019 Jul 29;58(31):10708-10712. doi: 10.1002/anie.201905601. Epub 2019 Jul 3.
6
Borylative cyclisation of diynes using BCl and borocations.使用BCl和硼正离子对二炔进行硼氢化环化反应。
Org Biomol Chem. 2019 Jun 5;17(22):5520-5525. doi: 10.1039/c9ob00991d.
7
Synthesis of a hydrogen-bridged tetraborane(6): a substituent effect of a diaminoboryl group toward the B-B multiple bond character.氢桥连四硼烷(6)的合成：二氨基硼基对B-B多重键特征的取代基效应
Dalton Trans. 2019 Apr 23;48(17):5496-5499. doi: 10.1039/c9dt01117j.
8
Consecutive intermolecular 1,1-carboboration reactions of MeSi-substituted alkynes with the halogeno-B(CF) reagents.甲基硅取代的炔烃与卤代硼（CF）试剂的连续分子间1,1-碳硼化反应。
Dalton Trans. 2019 Apr 9;48(15):4837-4845. doi: 10.1039/c9dt00413k.
9
Earth-Abundant Transition Metal Catalysts for Alkene Hydrosilylation and Hydroboration: Opportunities and Assessments.用于烯烃硅氢化和硼氢化反应的地球丰富型过渡金属催化剂：机遇与评估
Nat Rev Chem. 2018 May;2(5):15-34. doi: 10.1038/s41570-018-0001-2. Epub 2018 Apr 27.
10
Alkenyl Boronates: Synthesis and Applications.烯基硼酸酯：合成与应用。
Chem Asian J. 2019 Feb 1;14(3):329-343. doi: 10.1002/asia.201801559. Epub 2019 Jan 16.