Suppr超能文献

钯催化实现α,α-二氟酮烯醇盐的苄基化反应。

Palladium Catalysis Enables Benzylation of α,α-Difluoroketone Enolates.

机构信息

Department of Medicinal Chemistry, The University of Kansas, 1251 Wescoe Hall Drive, Lawrence, KS, 66045, USA.

Department of Medicinal Chemistry, Faculty of Pharmacy, Tehran University of Medical Science, 16 Azar St., Tehran, 1417614411, Iran.

出版信息

Angew Chem Int Ed Engl. 2016 Jul 25;55(31):9080-3. doi: 10.1002/anie.201604149. Epub 2016 Jun 17.

Abstract

A palladium-catalyzed decarboxylative benzylation reaction of α,α-difluoroketone enolates is reported, in which the key C(α)-C(sp(3) ) bond is generated by reductive elimination from a palladium intermediate. The transformation provides convergent access to α-benzyl-α,α-difluoroketone-based products, and should be useful for accessing biological probes.

摘要

本文报道了钯催化的α,α-二氟酮烯醇化物的脱羧苄基化反应,其中关键的 C(α)-C(sp(3) )键是通过钯中间体的还原消除生成的。该转化提供了一种收敛的方法来合成基于α-苄基-α,α-二氟酮的产物,这对于获得生物探针应该是有用的。

相似文献

1
Palladium Catalysis Enables Benzylation of α,α-Difluoroketone Enolates.
Angew Chem Int Ed Engl. 2016 Jul 25;55(31):9080-3. doi: 10.1002/anie.201604149. Epub 2016 Jun 17.
2
A general Pd-catalyzed α- and γ-benzylation of aldehydes for the formation of quaternary centers.
Org Biomol Chem. 2015 Jun 14;13(22):6338-43. doi: 10.1039/c5ob00702j.
3
Palladium-catalyzed carbonylative Negishi-type coupling of aryl iodides with benzyl chlorides.
Chem Asian J. 2012 Jan 2;7(1):40-4. doi: 10.1002/asia.201100627. Epub 2011 Oct 11.
5
Palladium-Catalyzed Enantioselective α-Arylation of α-Fluoroketones.
J Am Chem Soc. 2016 Dec 14;138(49):15980-15986. doi: 10.1021/jacs.6b09580. Epub 2016 Dec 1.
6
Ligand-controlled regiodivergent palladium-catalyzed decarboxylative allylation reaction to access α,α-difluoroketones.
Angew Chem Int Ed Engl. 2015 Feb 16;54(8):2361-5. doi: 10.1002/anie.201410039. Epub 2015 Jan 7.
8
Catalytic C-H allylation and benzylation of pyrazoles.
J Org Chem. 2015 Jan 2;80(1):690-7. doi: 10.1021/jo5025317. Epub 2014 Dec 17.
9
Palladium-catalyzed decarboxylative benzylation of diphenylglycinate imines.
Org Lett. 2010 Jan 15;12(2):316-9. doi: 10.1021/ol902651j.
10
Synthesis of aryl ketones by palladium(II)-catalyzed decarboxylative addition of benzoic acids to nitriles.
Angew Chem Int Ed Engl. 2010 Oct 11;49(42):7733-7. doi: 10.1002/anie.201003009.

引用本文的文献

1
Cobalt-catalyzed decarboxylative difluoroalkylation of nitrophenylacetic acid salts.
Chem Sci. 2023 Nov 16;14(47):13902-13907. doi: 10.1039/d3sc05583c. eCollection 2023 Dec 6.
2
Palladium-Catalyzed Dearomatization of Benzothiophenes: Isolation and Functionalization of a Discrete Dearomatized Intermediate.
Synthesis (Stuttg). 2023 Nov;55(21):3568-3574. doi: 10.1055/a-2092-9012. Epub 2023 Jun 13.
4
Decarbonylative Fluoroalkylation at Palladium(II): From Fundamental Organometallic Studies to Catalysis.
J Am Chem Soc. 2021 Nov 10;143(44):18617-18625. doi: 10.1021/jacs.1c08551. Epub 2021 Oct 28.
5
Nickel-Catalyzed Decarbonylative Synthesis of Fluoroalkyl Thioethers.
ACS Catal. 2020 Aug 7;10(15):8315-8320. doi: 10.1021/acscatal.0c02950. Epub 2020 Jul 17.

本文引用的文献

1
Ligand-controlled regiodivergent palladium-catalyzed decarboxylative allylation reaction to access α,α-difluoroketones.
Angew Chem Int Ed Engl. 2015 Feb 16;54(8):2361-5. doi: 10.1002/anie.201410039. Epub 2015 Jan 7.
2
Pd-catalyzed α-arylation of α,α-difluoroketones with aryl bromides and chlorides. A route to difluoromethylarenes.
J Am Chem Soc. 2014 Mar 19;136(11):4149-52. doi: 10.1021/ja501117v. Epub 2014 Mar 10.
3
Structure and reactivity of late transition metal η³-benzyl complexes.
Angew Chem Int Ed Engl. 2014 Mar 10;53(11):2826-51. doi: 10.1002/anie.201305972. Epub 2014 Feb 19.
4
Evaluation of difluoromethyl ketones as agonists of the γ-aminobutyric acid type B (GABAB) receptor.
J Med Chem. 2013 Mar 28;56(6):2456-65. doi: 10.1021/jm301805e. Epub 2013 Mar 6.
5
Dialkylbiaryl Phosphines in Pd-Catalyzed Amination: A User's Guide.
Chem Sci. 2011;2(1):27-50. doi: 10.1039/C0SC00331J.
6
Organocatalytic asymmetric synthesis of 3-difluoroalkyl 3-hydroxyoxindoles.
Chem Commun (Camb). 2012 Feb 11;48(13):1919-21. doi: 10.1039/c2cc17140f. Epub 2012 Jan 9.
7
Transition metal-catalyzed decarboxylative allylation and benzylation reactions.
Chem Rev. 2011 Mar 9;111(3):1846-913. doi: 10.1021/cr1002744. Epub 2011 Jan 14.
8
Decarboxylative benzylations of alkynes and ketones.
J Am Chem Soc. 2010 Jul 14;132(27):9280-2. doi: 10.1021/ja1035557.

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