Suppr超能文献

钯催化的带有 tethered 芳基/烯基三氟甲磺酸酯的烯烃的 C-C、C-N 和 C-O 键形成双官能团化反应

Pd-Catalyzed C-C, C-N, and C-O Bond-Forming Difunctionalization Reactions of Alkenes Bearing Tethered Aryl/Alkenyl Triflates.

作者信息

White Derick R, Bornowski Evan C, Wolfe John P

机构信息

Derick R. White, Evan C. Bornowski, John P. Wolfe Department of Chemistry, University of Michigan 930 N. University Ave., Ann Arbor, MI, 48109-1055, USA.

出版信息

Isr J Chem. 2020 Mar;60(3-4):259-267. doi: 10.1002/ijch.201900108. Epub 2020 Jan 24.

Abstract

Over the past few years our group has described a new type of alkene difunctionalization reaction in which aryl or alkenyl triflates bearing tethered alkenes are coupled with various nucleophiles to afford carbocyclic products. The products are formed in moderate to good chemical yield, with generally high levels of stereoselectivity. Our progress to date in this area, which includes reactions of amine, alcohol, enolate, and indole nucleophiles, is described in this review.

摘要

在过去几年中,我们团队描述了一种新型的烯烃双官能团化反应,其中带有连接烯烃的芳基或烯基三氟甲磺酸酯与各种亲核试剂偶联,以得到碳环产物。产物以中等至良好的化学产率形成,通常具有较高的立体选择性水平。本综述描述了我们迄今为止在该领域的进展,包括胺、醇、烯醇盐和吲哚亲核试剂的反应。

相似文献

1
Pd-Catalyzed C-C, C-N, and C-O Bond-Forming Difunctionalization Reactions of Alkenes Bearing Tethered Aryl/Alkenyl Triflates.
Isr J Chem. 2020 Mar;60(3-4):259-267. doi: 10.1002/ijch.201900108. Epub 2020 Jan 24.
3
Pd-Catalyzed Alkene Difunctionalization Reactions of Enolates for the Synthesis of Substituted Bicyclic Cyclopentanes.
Org Process Res Dev. 2019 Aug 16;23(8):1610-1630. doi: 10.1021/acs.oprd.9b00248. Epub 2019 Jul 30.
4
Palladium-Catalyzed Alkene Carboalkoxylation Reactions of Phenols and Alcohols for the Synthesis of Carbocycles.
Org Lett. 2017 Aug 18;19(16):4311-4314. doi: 10.1021/acs.orglett.7b01975. Epub 2017 Aug 8.
7
Palladium-Catalyzed Alkene Carboamination Reactions of Electron-Poor Nitrogen Nucleophiles.
Adv Synth Catal. 2015 Jul 6;357(10):2339-2344. doi: 10.1002/adsc.201500334. Epub 2015 Jul 14.
8
Palladium(II)-Catalyzed Oxidative Difunctionalization of Alkenes: Bond Forming at a High-Valent Palladium Center.
Acc Chem Res. 2016 Nov 15;49(11):2413-2423. doi: 10.1021/acs.accounts.6b00328. Epub 2016 Oct 14.
10
Transition Metal (Ni, Cu, Pd)-Catalyzed Alkene Dicarbofunctionalization Reactions.
Acc Chem Res. 2021 Sep 7;54(17):3415-3437. doi: 10.1021/acs.accounts.1c00329. Epub 2021 Aug 12.

引用本文的文献

1
Synthesis of 2-Cyanomethyl Indane Derivatives via Pd-Catalyzed Alkene Difunctionalization Reactions of Alkyl Nitriles.
Org Lett. 2023 Apr 28;25(16):2767-2770. doi: 10.1021/acs.orglett.3c00571. Epub 2023 Apr 18.
2
Oxidatively induced reactivity in Rh(iii)-catalyzed 7-azaindole synthesis: insights into the role of the silver additive.
Chem Sci. 2022 Aug 31;13(36):10707-10714. doi: 10.1039/d2sc01650h. eCollection 2022 Sep 21.
4
Highly Regio- and Diastereoselective Tethered Aza-Wacker Cyclizations of Alkenyl Phosphoramidates.
J Org Chem. 2021 Nov 5;86(21):14732-14758. doi: 10.1021/acs.joc.1c01483. Epub 2021 Oct 19.

本文引用的文献

1
Pd-Catalyzed Alkene Difunctionalization Reactions of Enolates for the Synthesis of Substituted Bicyclic Cyclopentanes.
Org Process Res Dev. 2019 Aug 16;23(8):1610-1630. doi: 10.1021/acs.oprd.9b00248. Epub 2019 Jul 30.
2
Stereocontrolled synthesis of bicyclic ureas and sulfamides via Pd-catalyzed alkene carboamination reactions.
Tetrahedron. 2019 Aug 9;75(32):4228-4243. doi: 10.1016/j.tet.2019.04.031. Epub 2019 Apr 20.
4
Pd-Catalyzed Alkene Carboheteroarylation Reactions for the Synthesis of 3-Cyclopentylindole Derivatives.
J Org Chem. 2018 Nov 2;83(21):13568-13573. doi: 10.1021/acs.joc.8b02165. Epub 2018 Oct 10.
5
Strategies toward Dicarbofunctionalization of Unactivated Olefins by Combined Heck Carbometalation and Cross-Coupling.
J Org Chem. 2018 Mar 16;83(6):3013-3022. doi: 10.1021/acs.joc.7b03128. Epub 2018 Mar 5.
6
Recent Developments in Pd(0)-Catalyzed Alkene Carboheterofunctionalization Reactions.
Asian J Org Chem. 2017 Jun;6(6):636-653. doi: 10.1002/ajoc.201600577. Epub 2017 Mar 10.
8
Palladium-Catalyzed Alkene Carboalkoxylation Reactions of Phenols and Alcohols for the Synthesis of Carbocycles.
Org Lett. 2017 Aug 18;19(16):4311-4314. doi: 10.1021/acs.orglett.7b01975. Epub 2017 Aug 8.
9
Synthesis of Cyclic Guanidines Bearing N-Arylsulfonyl and N-Cyano Protecting Groups via Pd-Catalyzed Alkene Carboamination Reactions.
Org Lett. 2017 Jun 2;19(11):2817-2820. doi: 10.1021/acs.orglett.7b00946. Epub 2017 May 23.
10
Stereocontrolled Synthesis of Amino-Substituted Carbocycles by Pd-Catalyzed Alkene Carboamination Reactions.
Chemistry. 2017 Apr 24;23(23):5419-5423. doi: 10.1002/chem.201700466. Epub 2017 Apr 3.

文献AI研究员

20分钟写一篇综述,助力文献阅读效率提升50倍。

立即体验

用中文搜PubMed

大模型驱动的PubMed中文搜索引擎

马上搜索

文档翻译

学术文献翻译模型,支持多种主流文档格式。

立即体验