三氟硼酸钾酮同烯醇盐的铃木-宫浦交叉偶联反应的范围
Scope of the Suzuki-Miyaura cross-coupling reaction of potassium trifluoroboratoketohomoenolates.
作者信息
Molander Gary A, Jean-Gérard Ludivine
机构信息
Roy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania 19104-6323, USA.
出版信息
J Org Chem. 2009 Feb 6;74(3):1297-303. doi: 10.1021/jo802453m.
Abstract
Potassium trifluoroboratoketohomoenolates were prepared in good yields from either the corresponding alpha,beta-unsaturated compounds or methyl ketones. These organoboron reagents were effectively cross-coupled with various aryl and heteroaryl chlorides.
摘要
三氟硼酸钾酮醇盐可由相应的α,β-不饱和化合物或甲基酮以良好的产率制备。这些有机硼试剂能有效地与各种芳基和杂芳基氯化物发生交叉偶联反应。
相似文献
1
Scope of the Suzuki-Miyaura cross-coupling reaction of potassium trifluoroboratoketohomoenolates.
J Org Chem. 2009 Feb 6;74(3):1297-303. doi: 10.1021/jo802453m.
2
Scope of aminomethylations via Suzuki-Miyaura cross-coupling of organotrifluoroborates.
J Org Chem. 2008 Mar 21;73(6):2052-7. doi: 10.1021/jo800183q. Epub 2008 Feb 20.
3
Suzuki-Miyaura cross-coupling of potassium trifluoroboratohomoenolates.
Org Lett. 2008 May 1;10(9):1795-8. doi: 10.1021/ol800357c. Epub 2008 Apr 8.
4
Use of potassium beta-trifluoroborato amides in Suzuki-Miyaura cross-coupling reactions.
J Org Chem. 2009 Aug 7;74(15):5446-50. doi: 10.1021/jo900968h.
5
Visible Light Photoredox Cross-Coupling of Acyl Chlorides with Potassium Alkoxymethyltrifluoroborates: Synthesis of α-Alkoxyketones.
Org Lett. 2016 Feb 19;18(4):732-5. doi: 10.1021/acs.orglett.5b03705. Epub 2016 Feb 1.
6
Cross-coupling of cyclopropyl- and cyclobutyltrifluoroborates with aryl and heteroaryl chlorides.
J Org Chem. 2008 Oct 3;73(19):7481-5. doi: 10.1021/jo801269m. Epub 2008 Aug 30.
7
Highly reactive, general, and long-lived catalysts for coupling heteroaryl and aryl chlorides with primary nitrogen nucleophiles.
Angew Chem Int Ed Engl. 2005 Feb 18;44(9):1371-5. doi: 10.1002/anie.200462629.
8
Palladium-catalyzed Suzuki-Miyaura cross-coupling reactions of enantiomerically enriched potassium β-trifluoroboratoamides with various aryl- and hetaryl chlorides.
Org Lett. 2010 Oct 1;12(19):4384-7. doi: 10.1021/ol101865e.
9
Synergistic Photoredox/Nickel Coupling of Acyl Chlorides with Secondary Alkyltrifluoroborates: Dialkyl Ketone Synthesis.
J Org Chem. 2017 Feb 3;82(3):1856-1863. doi: 10.1021/acs.joc.6b02897. Epub 2017 Jan 17.
10
Ether-imidazolium carbenes for Suzuki-Miyaura cross-coupling of heteroaryl chlorides with aryl/heteroarylboron reagents.
Org Lett. 2013 Jun 7;15(11):2716-9. doi: 10.1021/ol4010189. Epub 2013 May 28.
引用本文的文献
1
Rapid, Homogenous, B-Alkyl Suzuki-Miyaura Cross-Coupling of Boronic Esters.
J Org Chem. 2024 Nov 15;89(22):16195-16202. doi: 10.1021/acs.joc.4c00089. Epub 2024 Mar 14.
2
Copper-catalyzed β-boration of α,β-unsaturated carbonyl compounds with tetrahydroxydiborane.
Org Lett. 2011 Sep 2;13(17):4684-7. doi: 10.1021/ol201900d. Epub 2011 Aug 5.
3
Metal-free chlorodeboronation of organotrifluoroborates.
J Org Chem. 2011 Sep 2;76(17):7195-203. doi: 10.1021/jo201313a. Epub 2011 Aug 3.
4
Studies of microwave-enhanced Suzuki-Miyaura vinylation of electron-rich sterically hindered substrates utilizing potassium vinyltrifluoroborate.
Tetrahedron Lett. 2010 Dec 22;51(51):6748-6752. doi: 10.1016/j.tetlet.2010.10.087.
5
Stereospecific cross-coupling of secondary alkyl β-trifluoroboratoamides.
J Am Chem Soc. 2010 Dec 8;132(48):17108-10. doi: 10.1021/ja108949w. Epub 2010 Nov 15.
6
Palladium-catalyzed Suzuki-Miyaura cross-coupling reactions of enantiomerically enriched potassium β-trifluoroboratoamides with various aryl- and hetaryl chlorides.
Org Lett. 2010 Oct 1;12(19):4384-7. doi: 10.1021/ol101865e.
7
Synthesis and carbohydrate binding studies of fluorescent alpha-amidoboronic acids and the corresponding bisboronic acids.
Bioorg Med Chem. 2010 Feb 15;18(4):1449-55. doi: 10.1016/j.bmc.2010.01.017. Epub 2010 Jan 11.
8
Organotrifluoroborates and monocoordinated palladium complexes as catalysts--a perfect combination for Suzuki-Miyaura coupling.
Angew Chem Int Ed Engl. 2009;48(49):9240-61. doi: 10.1002/anie.200904306.
9
Potassium trifluoroborate salts as convenient, stable reagents for difficult alkyl transfers.
Curr Opin Drug Discov Devel. 2009 Nov;12(6):811-23.
10
Use of potassium beta-trifluoroborato amides in Suzuki-Miyaura cross-coupling reactions.
J Org Chem. 2009 Aug 7;74(15):5446-50. doi: 10.1021/jo900968h.
本文引用的文献
1
Preparation of potassium alkoxymethyltrifluoroborates and their cross-coupling with aryl chlorides.
Org Lett. 2008 Jun 5;10(11):2135-8. doi: 10.1021/ol800532p. Epub 2008 Apr 26.
2
Suzuki-Miyaura cross-coupling of potassium trifluoroboratohomoenolates.
Org Lett. 2008 May 1;10(9):1795-8. doi: 10.1021/ol800357c. Epub 2008 Apr 8.
3
Scope of aminomethylations via Suzuki-Miyaura cross-coupling of organotrifluoroborates.
J Org Chem. 2008 Mar 21;73(6):2052-7. doi: 10.1021/jo800183q. Epub 2008 Feb 20.
4
Potassium organotrifluoroborates: new perspectives in organic synthesis.
Chem Rev. 2008 Jan;108(1):288-325. doi: 10.1021/cr0509758. Epub 2007 Dec 21.
5
Nickel-catalyzed beta-boration of alpha,beta-unsaturated esters and amides with bis(pinacolato)diboron.
Org Lett. 2007 Nov 22;9(24):5031-3. doi: 10.1021/ol702254g. Epub 2007 Nov 1.
6
Scope of the Suzuki-Miyaura aminoethylation reaction using organotrifluoroborates.
J Org Chem. 2007 Oct 26;72(22):8422-6. doi: 10.1021/jo7015955. Epub 2007 Oct 4.
7
Total syntheses of 2,2'-epi-cytoskyrin A, rugulosin, and the alleged structure of rugulin.
J Am Chem Soc. 2007 Apr 4;129(13):4001-13. doi: 10.1021/ja0685708. Epub 2007 Mar 14.
8
Organotrifluoroborates: protected boronic acids that expand the versatility of the Suzuki coupling reaction.
Acc Chem Res. 2007 Apr;40(4):275-86. doi: 10.1021/ar050199q. Epub 2007 Jan 26.
9
Copper-catalyzed beta-Boration of alpha,beta-unsaturated carbonyl compounds: rate acceleration by alcohol additives.
Org Lett. 2006 Oct 12;8(21):4887-9. doi: 10.1021/ol061955a.
10
Palladium-catalyzed Suzuki-Miyaura cross-coupling reactions of potassium aryl- and heteroaryltrifluoroborates.
J Org Chem. 2003 May 30;68(11):4302-14. doi: 10.1021/jo0342368.
Zotero 插件