• 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

导向镍催化的烯基羰基化合物的1,2-二烷基化反应

Directed nickel-catalyzed 1,2-dialkylation of alkenyl carbonyl compounds.

作者信息

Derosa Joseph, van der Puyl Vincent A, Tran Van T, Liu Mingyu, Engle Keary M

机构信息

Department of Chemistry , The Scripps Research Institute , 10550 North Torrey Pines Road , La Jolla , California 92037 , USA . Email:

出版信息

Chem Sci. 2018 May 16;9(23):5278-5283. doi: 10.1039/c8sc01735b. eCollection 2018 Jun 21.

DOI:10.1039/c8sc01735b
PMID:29997883
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC6001383/
Abstract

A nickel-catalyzed conjunctive cross-coupling of non-conjugated alkenes, alkyl halides, and alkylzinc reagents is reported. Regioselectivity is controlled by chelation of a removable bidentate 8-aminoquinoline directing group. Under optimized conditions, a wide range of 1,2-dialkylated products can be accessed in moderate to excellent yields. To the best of our knowledge, this report represents the first example of three-component 1,2-dialkylation of non-conjugated alkenes to introduce differentiated alkyl fragments.

摘要

报道了一种镍催化的非共轭烯烃、卤代烃和烷基锌试剂的联合交叉偶联反应。区域选择性由可移除的双齿8-氨基喹啉导向基团的螯合作用控制。在优化条件下,可以以中等至优异的产率获得多种1,2-二烷基化产物。据我们所知,本报告代表了非共轭烯烃的三组分1,2-二烷基化以引入不同烷基片段的首个实例。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7a33/6001383/16c59cb0646b/c8sc01735b-s4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7a33/6001383/efafdfbf3ad6/c8sc01735b-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7a33/6001383/e4db09da4d08/c8sc01735b-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7a33/6001383/9f54c7afe2e7/c8sc01735b-s3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7a33/6001383/16c59cb0646b/c8sc01735b-s4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7a33/6001383/efafdfbf3ad6/c8sc01735b-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7a33/6001383/e4db09da4d08/c8sc01735b-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7a33/6001383/9f54c7afe2e7/c8sc01735b-s3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7a33/6001383/16c59cb0646b/c8sc01735b-s4.jpg

相似文献

1
Directed nickel-catalyzed 1,2-dialkylation of alkenyl carbonyl compounds.导向镍催化的烯基羰基化合物的1,2-二烷基化反应
Chem Sci. 2018 May 16;9(23):5278-5283. doi: 10.1039/c8sc01735b. eCollection 2018 Jun 21.
2
Nickel-Catalyzed β,γ-Dicarbofunctionalization of Alkenyl Carbonyl Compounds via Conjunctive Cross-Coupling.镍催化的烯基羰基化合物的β,γ-双官能团化通过共轭交叉偶联反应。
J Am Chem Soc. 2017 Aug 9;139(31):10657-10660. doi: 10.1021/jacs.7b06567. Epub 2017 Jul 28.
3
Nickel-Catalyzed 8-Aminoquinoline Directed Reductive Dialkylcyclization/Homodialkylation of Unactivated Alkenes.镍催化8-氨基喹啉导向的未活化烯烃的还原二烷基环化/同二烷基化反应
Org Lett. 2023 Nov 3;25(43):7800-7804. doi: 10.1021/acs.orglett.3c02955. Epub 2023 Oct 24.
4
Directed, nickel-catalyzed 1,2-alkylsulfenylation of alkenyl carbonyl compounds.导向的镍催化烯基羰基化合物的1,2-烷基硫醚化反应。
Chem Sci. 2022 May 2;13(22):6567-6572. doi: 10.1039/d2sc01563c. eCollection 2022 Jun 7.
5
Ni-Catalyzed Regioselective 1,2-Dialkylation of Alkenes Enabled by the Formation of Two C(sp)-C(sp) Bonds.镍催化的通过形成两个 C(sp)-C(sp)键实现的烯烃的区域选择性 1,2-二烷基化反应。
J Am Chem Soc. 2020 Dec 16;142(50):20930-20936. doi: 10.1021/jacs.0c09778. Epub 2020 Dec 3.
6
A Sterically Tuned Directing Auxiliary Promotes Catalytic 1,2-Carbofluorination of Alkenyl Carbonyl Compounds.位阻调控导向辅助促进烯基羰基化合物的催化 1,2-碳氟键形成反应。
Angew Chem Int Ed Engl. 2023 Jan 23;62(4):e202214153. doi: 10.1002/anie.202214153. Epub 2022 Dec 15.
7
Nickel-Catalyzed Reductive Alkene Cross-Dialkylation with Unactivated Alkyl Electrophiles.镍催化未活化烷基亲电试剂的还原烯烃交叉二烷基化反应
Org Lett. 2024 Feb 16;26(6):1190-1195. doi: 10.1021/acs.orglett.3c04207. Epub 2024 Feb 3.
8
Ni-Catalyzed Reductive 1,2-Cross-Dialkylation of Unactivated Alkenes with Two Alkyl Bromides.镍催化的未活化烯烃与两个溴代烷基的 1,2-交叉二烷基化反应。
Org Lett. 2022 Jun 3;24(21):3844-3849. doi: 10.1021/acs.orglett.2c01416. Epub 2022 May 20.
9
Nickel-Catalyzed Regioselective Intermolecular Dialkylation of Alkenylarenes: Generation of Two Vicinal C(sp )-C(sp ) Bonds Across Alkenes.镍催化的烯基芳烃区域选择性分子间二烷基化反应:通过烯烃生成两个相邻的C(sp³)-C(sp³)键
Angew Chem Int Ed Engl. 2023 Aug 7;62(32):e202305522. doi: 10.1002/anie.202305522. Epub 2023 Jun 29.
10
Synthesis of E-Alkyl Alkenes from Terminal Alkynes via Ni-Catalyzed Cross-Coupling of Alkyl Halides with B-Alkenyl-9-borabicyclo[3.3.1]nonanes.通过镍催化卤代烃与β-烯基-9-硼双环[3.3.1]壬烷的交叉偶联反应从末端炔烃合成E-烷基烯烃
Org Lett. 2015 Oct 2;17(19):4910-3. doi: 10.1021/acs.orglett.5b02482.

引用本文的文献

1
Ruthenium-catalyzed three-component tandem remote C-H functionalization of naphthalenes: modular and concise synthesis of multifunctional naphthalenes.钌催化萘的三组分串联远程C-H官能团化反应:多功能萘的模块化简洁合成
Chem Sci. 2024 Dec 12;16(4):1957-1965. doi: 10.1039/d4sc06846g. eCollection 2025 Jan 22.
2
Cobalt-catalyzed conformationally restricted alkylarylation enables divergent access to Csp-rich N-heterocycles.钴催化的构象受限烷基芳基化反应能够以不同方式合成富含Csp的氮杂环化合物。
Chem Sci. 2024 Sep 3;15(39):16250-8. doi: 10.1039/d4sc04056b.
3
Directed copper-catalyzed C-H functionalization of unactivated olefins with azodicarbonamide compounds.

本文引用的文献

1
Ni-catalysed regioselective 1,2-diarylation of unactivated olefins by stabilizing Heck intermediates as pyridylsilyl-coordinated transient metallacycles.通过将 Heck 中间体稳定为吡啶基硅烷基配位的瞬态金属环,实现镍催化的未活化烯烃的区域选择性 1,2-二芳基化反应。
Chem Sci. 2017 Nov 27;9(4):904-909. doi: 10.1039/c7sc04351a. eCollection 2018 Jan 28.
2
Nickel-catalyzed difunctionalization of allyl moieties using organoboronic acids and halides with divergent regioselectivities.镍催化烯丙基部分与有机硼酸和卤化物的双官能化反应,具有不同的区域选择性。
Chem Sci. 2017 Oct 26;9(3):600-607. doi: 10.1039/c7sc03149a. eCollection 2018 Jan 21.
3
铜催化未活化烯烃与偶氮二甲酰胺化合物的定向C-H官能化反应
RSC Adv. 2024 Aug 29;14(38):27475-27480. doi: 10.1039/d4ra04113e.
4
Harnessing Bromo/Acyloxy Transposition (BrAcT) and Excited-State Copper Catalysis for Styrene Difunctionalization.利用溴代/酰氧基转位反应(BrAcT)和激发态铜催化实现苯乙烯的双官能化反应。
J Am Chem Soc. 2024 Aug 7;146(31):21271-21279. doi: 10.1021/jacs.4c08984. Epub 2024 Jul 23.
5
Congested C(sp3)-rich architectures enabled by iron-catalysed conjunctive alkylation.铁催化的联合烷基化实现富C(sp3)的密集结构
Nat Catal. 2024 Mar;7(3):321-329. doi: 10.1038/s41929-024-01113-8. Epub 2024 Feb 23.
6
Iron-Mediated Dialkylation of Alkenylarenes with Benzyl Bromides.铁介导的烯基芳烃与苄基溴的双烷基化反应
J Org Chem. 2024 Nov 15;89(22):16292-16299. doi: 10.1021/acs.joc.3c02548. Epub 2024 Apr 4.
7
Alkene dialkylation by triple radical sorting.三重自由基分类法进行烯烃的二烷基化。
Nature. 2024 Apr;628(8006):104-109. doi: 10.1038/s41586-024-07165-x. Epub 2024 Feb 13.
8
Ni-Catalyzed Regio- and Stereoselective Alkylarylation of Unactivated Alkenes in γ,δ-Alkenylketimines.镍催化γ,δ-烯基酮亚胺中未活化烯烃的区域和立体选择性烷基芳基化反应
ACS Catal. 2022 Jun 17;12(12):7262-7268. doi: 10.1021/acscatal.2c01697. Epub 2022 Jun 2.
9
Three-Component Cross-Electrophile Coupling: Regioselective Electrochemical Dialkylation of Alkenes.三组分交叉亲电试剂偶联反应:烯烃的区域选择性电化学二烷基化反应
J Am Chem Soc. 2023 Oct 18;145(41):22298-22304. doi: 10.1021/jacs.3c06794. Epub 2023 Oct 6.
10
Salt-stabilized alkylzinc pivalates: versatile reagents for cobalt-catalyzed selective 1,2-dialkylation.盐稳定的新戊酸烷基锌:钴催化选择性1,2 - 二烷基化的通用试剂
Chem Sci. 2023 Jul 26;14(32):8672-8680. doi: 10.1039/d3sc02345a. eCollection 2023 Aug 16.
Transition Metal-Catalyzed Dicarbofunctionalization of Unactivated Olefins.
过渡金属催化的非活化烯烃双官能化反应。
Chem Rec. 2018 Sep;18(9):1314-1340. doi: 10.1002/tcr.201700098. Epub 2018 Mar 8.
4
Strategies toward Dicarbofunctionalization of Unactivated Olefins by Combined Heck Carbometalation and Cross-Coupling.通过 Heck 碳金属化和交叉偶联联合作用实现未活化烯烃的双官能化策略。
J Org Chem. 2018 Mar 16;83(6):3013-3022. doi: 10.1021/acs.joc.7b03128. Epub 2018 Mar 5.
5
Ni-Catalyzed Regioselective Dicarbofunctionalization of Unactivated Olefins by Tandem Cyclization/Cross-Coupling and Application to the Concise Synthesis of Lignan Natural Products.镍催化的未活化烯烃的区域选择性双官能化反应:串联环化/交叉偶联反应及其在木脂素天然产物的简洁合中的应用。
J Org Chem. 2018 Mar 2;83(5):2920-2936. doi: 10.1021/acs.joc.8b00184. Epub 2018 Feb 22.
6
Ni-Catalyzed Enantioselective Conjunctive Coupling with C(sp) Electrophiles: A Radical-Ionic Mechanistic Dichotomy.镍催化的 C(sp) 亲电试剂对映选择性偶联反应:自由基-离子机理二分法。
J Am Chem Soc. 2017 Dec 6;139(48):17293-17296. doi: 10.1021/jacs.7b10519. Epub 2017 Nov 20.
7
Tridentate Directing Groups Stabilize 6-Membered Palladacycles in Catalytic Alkene Hydrofunctionalization.三齿导向基团稳定催化烯烃氢官能化反应中的六元钯环。
J Am Chem Soc. 2017 Nov 8;139(44):15576-15579. doi: 10.1021/jacs.7b08383. Epub 2017 Oct 26.
8
Nickel-Catalyzed β,γ-Dicarbofunctionalization of Alkenyl Carbonyl Compounds via Conjunctive Cross-Coupling.镍催化的烯基羰基化合物的β,γ-双官能团化通过共轭交叉偶联反应。
J Am Chem Soc. 2017 Aug 9;139(31):10657-10660. doi: 10.1021/jacs.7b06567. Epub 2017 Jul 28.
9
Ni-Catalyzed Regioselective 1,2-Dicarbofunctionalization of Olefins by Intercepting Heck Intermediates as Imine-Stabilized Transient Metallacycles.镍催化的通过捕获 Heck 中间体作为亚胺稳定的瞬态金属环来实现烯烃的区域选择性 1,2-双官能化反应。
J Am Chem Soc. 2017 Aug 9;139(31):10653-10656. doi: 10.1021/jacs.7b06340. Epub 2017 Jul 26.
10
Nickel-Catalyzed Reductive Dicarbofunctionalization of Alkenes.镍催化烯烃的还原双官能团化反应。
J Am Chem Soc. 2017 May 24;139(20):6835-6838. doi: 10.1021/jacs.7b03195. Epub 2017 May 10.