钯（0）催化的通过偕烯丙基和芳基 C-H 胺化的 α-甲基苯乙烯的顺序 C-N 键形成与重氮酮。
Pd(0)-catalyzed sequential C-N bond formation via allylic and aromatic C-H amination of α-methylstyrenes with diaziridinone.
机构信息
Department of Chemistry, Colorado State University, Fort Collins, Colorado 80523, USA.
出版信息
Org Lett. 2013 Aug 16;15(16):4210-3. doi: 10.1021/ol401935c. Epub 2013 Aug 6.
Abstract
A novel Pd(0)-catalyzed sequential C-N bond formation process via allylic and aromatic C-H amination of α-methylstyrenes with di-tert-butyldiaziridinone, giving spirocyclic indolines in good yields, is described. Four C-N bonds and one spiro quaternary carbon are generated in a single operation.
摘要
一种新型的 Pd(0)-催化的顺序 C-N 键形成过程，通过烯丙基和芳香族 C-H 胺化α-甲基苯乙烯与二叔丁基二氮杂环丁酮，以良好的收率得到螺环吲哚啉，在单一操作中生成四个 C-N 键和一个螺季碳。
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本文引用的文献
1
The Chemistry of Vicinal Diamines.
Angew Chem Int Ed Engl. 1998 Oct 16;37(19):2580-2627. doi: 10.1002/(SICI)1521-3773(19981016)37:19<2580::AID-ANIE2580>3.0.CO;2-L.
2
Transition Metal Catalyzed Coupling Reactions under C-H Activation.
Angew Chem Int Ed Engl. 1999 Jun 14;38(12):1698-1712. doi: 10.1002/(SICI)1521-3773(19990614)38:12<1698::AID-ANIE1698>3.0.CO;2-6.
3
Synthesis of indolines via Pd(II)-catalyzed amination of C-H bonds using PhI(OAc)2 as the bystanding oxidant.
Org Lett. 2013 Jun 21;15(12):3058-61. doi: 10.1021/ol401246u. Epub 2013 May 31.
4
A convenient synthesis of anthranilic acids by Pd-catalyzed direct intermolecular ortho-C-H amidation of benzoic acids.
Chem Commun (Camb). 2012 Dec 11;48(95):11680-2. doi: 10.1039/c2cc36502b.
5
Methods for direct alkene diamination, new & old.
Tetrahedron. 2012 Jun 3;68(22):4067-4105. doi: 10.1016/j.tet.2012.03.036. Epub 2012 Mar 21.
6
Improved protocol for indoline synthesis via palladium-catalyzed intramolecular C(sp2)-H amination.
Org Lett. 2012 Jun 15;14(12):2944-7. doi: 10.1021/ol301352v. Epub 2012 Jun 6.
7
Metal-catalyzed nitrogen-atom transfer methods for the oxidation of aliphatic C-H bonds.
Acc Chem Res. 2012 Jun 19;45(6):911-22. doi: 10.1021/ar200318q. Epub 2012 Apr 30.
8
C-C, C-O and C-N bond formation via rhodium(III)-catalyzed oxidative C-H activation.
Chem Soc Rev. 2012 May 7;41(9):3651-78. doi: 10.1039/c2cs15281a. Epub 2012 Feb 29.
9
Chiral monodentate phosphines and bulky carboxylic acids: cooperative effects in palladium-catalyzed enantioselective C(sp3)-H functionalization.
Angew Chem Int Ed Engl. 2012 Feb 27;51(9):2238-42. doi: 10.1002/anie.201108511. Epub 2012 Feb 3.
10
Highly efficient syntheses of azetidines, pyrrolidines, and indolines via palladium catalyzed intramolecular amination of C(sp3)-H and C(sp2)-H bonds at γ and δ positions.
J Am Chem Soc. 2012 Jan 11;134(1):3-6. doi: 10.1021/ja210660g. Epub 2011 Dec 29.
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