Suppr超能文献

镍催化的1,3-二烯对映选择性氢官能团化反应

Ni-Catalyzed Enantioselective Hydrofunctionalizations of 1,3-Dienes.

作者信息

Flaget Arthur, Zhang Cheng, Mazet Clément

机构信息

Department of Organic Chemistry, University of Geneva, 30 quai Ernest Ansermet, 1211 Geneva, Switzerland.

出版信息

ACS Catal. 2022 Dec 16;12(24):15638-15647. doi: 10.1021/acscatal.2c05251. Epub 2022 Dec 6.

Abstract

Ni-catalyzed enantioselective hydrofunctionalizations of conjugated dienes are particularly demanding reactions to devise because they require not only addressing the inherent challenges associated with the development of an enantioselective transformation but also overcoming all other aspects of selective catalysis (chemoselectivity, regioselectivity, diastereoselectivity, etc.). However, the value-added nature of the chiral allylic and homoallylic derivatives obtained by these methods, the lack of efficient alternatives, and the use of an earth-abundant first-row transition metal have led to renewed interest over the past decade. In this Perspective, we give an overview of the developments in this field, from the original findings (often dating back to the last century) to the most recent contributions. Emphasis is placed on the nature of the hydrofunctionalization agent (C(sp), C(sp), C(sp), N, P, or O).

摘要

镍催化共轭二烯的对映选择性氢官能团化反应是特别具有挑战性的反应,因为它们不仅需要解决与对映选择性转化发展相关的固有挑战,还需要克服选择性催化的所有其他方面(化学选择性、区域选择性、非对映选择性等)。然而,通过这些方法获得的手性烯丙基和高烯丙基衍生物的高附加值性质、缺乏有效的替代方法以及使用储量丰富的第一排过渡金属,在过去十年中引发了新的兴趣。在这篇综述中,我们概述了该领域的发展,从最初的发现(通常可追溯到上世纪)到最新的研究成果。重点放在氢官能团化试剂的性质(C(sp)、C(sp)、C(sp)、N、P或O)上。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8354/9765749/a0056ccca4dc/cs2c05251_0001.jpg

相似文献

1
Ni-Catalyzed Enantioselective Hydrofunctionalizations of 1,3-Dienes.
ACS Catal. 2022 Dec 16;12(24):15638-15647. doi: 10.1021/acscatal.2c05251. Epub 2022 Dec 6.
3
Iron- and Cobalt-Catalyzed Asymmetric Hydrofunctionalization of Alkenes and Alkynes.
Acc Chem Res. 2021 Jun 1;54(11):2701-2716. doi: 10.1021/acs.accounts.1c00212. Epub 2021 May 19.
5
Ligand-Dictated Regiodivergent Allylic Functionalizations via Palladium-Catalyzed Remote Substitution.
Angew Chem Int Ed Engl. 2023 Jul 10;62(28):e202301556. doi: 10.1002/anie.202301556. Epub 2023 Apr 7.
6
Palladium-Catalyzed Asymmetric Allylic C-H Functionalization: Mechanism, Stereo- and Regioselectivities, and Synthetic Applications.
Acc Chem Res. 2020 Dec 15;53(12):2841-2854. doi: 10.1021/acs.accounts.0c00477. Epub 2020 Oct 2.
9
Coordination Assistance: A Powerful Strategy for Metal-Catalyzed Regio- and Enantioselective Hydroalkynylation of Internal Alkenes.
Acc Chem Res. 2023 Feb 7;56(3):308-321. doi: 10.1021/acs.accounts.2c00713. Epub 2023 Jan 11.
10
Mechanism and Selectivity Control in Ni- and Pd-Catalyzed Cross-Couplings Involving Carbon-Oxygen Bond Activation.
Acc Chem Res. 2021 May 4;54(9):2158-2171. doi: 10.1021/acs.accounts.1c00050. Epub 2021 Apr 7.

引用本文的文献

3
Rh-catalysed single-carbon insertion to 1,3-dienes.
Chem Sci. 2025 Jun 19. doi: 10.1039/d5sc03161c.
4
Direct Synthesis of Allylic Sulfones via Hydrosulfonylation of 1,3-Dienes with Sulfinic Acids.
Molecules. 2025 Apr 16;30(8):1785. doi: 10.3390/molecules30081785.
6
Access to Cyclic Borates by Cu-Catalyzed Borylation of Unactivated Vinylcyclopropanes.
Org Lett. 2024 Jun 28;26(25):5386-5390. doi: 10.1021/acs.orglett.4c01938. Epub 2024 Jun 13.
7
Understanding the Regiodivergence between Hydroarylation and Trifluoromethylarylation of 1,3-Dienes Using Anilines in HFIP.
JACS Au. 2024 May 10;4(5):1744-1751. doi: 10.1021/jacsau.4c00162. eCollection 2024 May 27.
8
Palladium-Catalyzed Regiodivergent Three-Component Alkenylamination of 1,3-Dienes with Alkyl and Aryl Amines.
J Am Chem Soc. 2023 Dec 20;145(50):27680-27689. doi: 10.1021/jacs.3c09873. Epub 2023 Dec 6.
9
Asymmetric formal sp-hydrocarbonations of dienes and alkynes via palladium hydride catalysis.
Nat Commun. 2023 Oct 9;14(1):6303. doi: 10.1038/s41467-023-42160-2.
10
Migratory allylic arylation of 1,n-enols enabled by nickel catalysis.
Nat Commun. 2023 Jun 7;14(1):3308. doi: 10.1038/s41467-023-38865-z.

本文引用的文献

1
Nickel-catalyzed regio- and enantio-selective Markovnikov hydromonofluoroalkylation of 1,3-dienes.
Chem Sci. 2022 Oct 11;13(42):12519-12526. doi: 10.1039/d2sc03958c. eCollection 2022 Nov 2.
2
Enantioselective C2-H Alkylation of Pyridines with 1,3-Dienes via Ni-Al Bimetallic Catalysis.
J Am Chem Soc. 2022 Oct 19;144(41):18810-18816. doi: 10.1021/jacs.2c09306. Epub 2022 Oct 7.
5
Ni-Catalyzed Regioselective Hydroarylation of 1-Aryl-1,3-Butadienes with Aryl Halides.
Chemistry. 2021 Nov 17;27(64):15903-15907. doi: 10.1002/chem.202102847. Epub 2021 Oct 1.
6
Regio-, Chemo-, and Enantioselective Ni-Catalyzed Hydrocyanation of 1,3-Dienes.
Org Lett. 2021 Feb 5;23(3):930-935. doi: 10.1021/acs.orglett.0c04133. Epub 2021 Jan 22.
7
Modern Synthetic Methods for the Stereoselective Construction of 1,3-Dienes.
Molecules. 2021 Jan 6;26(2):249. doi: 10.3390/molecules26020249.
8
Mechanistic Studies of Nickel-Catalyzed Hydroarylation of Styrenes.
Org Lett. 2020 Nov 20;22(22):8998-9003. doi: 10.1021/acs.orglett.0c03395. Epub 2020 Nov 4.
9
Ni-Catalyzed Regiodivergent and Stereoselective Hydroalkylation of Acyclic Branched Dienes with Unstabilized C(sp) Nucleophiles.
J Am Chem Soc. 2020 Sep 23;142(38):16486-16492. doi: 10.1021/jacs.0c08319. Epub 2020 Sep 14.
10
Enantioselective Synthesis of Functionalized Arenes by Nickel-Catalyzed Site-Selective Hydroarylation of 1,3-Dienes with Aryl Boronates.
Angew Chem Int Ed Engl. 2020 Aug 10;59(33):14070-14075. doi: 10.1002/anie.202004982. Epub 2020 Jun 4.

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