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Literature DB >> 15771482

Highly efficient copper-catalyzed nitro-Mannich type reaction: cross-dehydrogenative-coupling between sp3 C-H bond and sp3 C-H bond.

Abstract

A novel C-C bond formation method was developed via the cross-dehydrogenative-coupling (CDC) reaction catalyzed by using copper bromide in the presence of an oxidizing reagent, tert-BuOOH. The CDC reaction provides a simple and efficient catalytic method to construct beta-nitroamine via the reaction between sp3 C-H and sp3 C-H bonds.

Entities: Chemical

Year: 2005 PMID： 15771482 DOI： 10.1021/ja050058j

Source DB: PubMed Journal: J Am Chem Soc ISSN： 0002-7863 Impact factor: 15.419

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Cited

27 in total

1. Functionally diverse nucleophilic trapping of iminium intermediates generated utilizing visible light.

Authors: David B Freeman; Laura Furst; Allison G Condie; Corey R J Stephenson
Journal: Org Lett Date: 2011-12-08 Impact factor: 6.005

2. The oxidative mannich reaction catalyzed by dirhodium caprolactamate.

Authors: Arthur J Catino; Jason M Nichols; Brian J Nettles; Michael P Doyle
Journal: J Am Chem Soc Date: 2006-05-03 Impact factor: 15.419

3. Cu-catalyzed cross-dehydrogenative coupling: a versatile strategy for C-C bond formations via the oxidative activation of sp(3) C-H bonds.

Authors: Zhiping Li; D Scott Bohle; Chao-Jun Li
Journal: Proc Natl Acad Sci U S A Date: 2006-06-05 Impact factor: 11.205

Review 4. Copper-Promoted Functionalization of Organic Molecules: from Biologically Relevant Cu/O₂ Model Systems to Organometallic Transformations.

Authors: Rachel Trammell; Khashayar Rajabimoghadam; Isaac Garcia-Bosch
Journal: Chem Rev Date: 2019-01-30 Impact factor: 60.622

9. Pd(OAc)(2)-catalyzed domino reactions of 1,2-dihaloarenes and 2-haloaryl arenesulfonates with Grignard reagents: efficient synthesis of substituted fluorenes.

Authors: Cheng-Guo Dong; Qiao-Sheng Hu
Journal: Tetrahedron Date: 2008-03-10 Impact factor: 2.457

10. α-Arylation of Saturated Azacycles and N-Methylamines via Palladium(II)-Catalyzed C(sp(3))-H Coupling.

Authors: Jillian E Spangler; Yoshihisa Kobayashi; Pritha Verma; Dong-Hui Wang; Jin-Quan Yu
Journal: J Am Chem Soc Date: 2015-09-10 Impact factor: 15.419

Highly efficient copper-catalyzed nitro-Mannich type reaction: cross-dehydrogenative-coupling between sp3 C-H bond and sp3 C-H bond.

1. Functionally diverse nucleophilic trapping of iminium intermediates generated utilizing visible light.

2. The oxidative mannich reaction catalyzed by dirhodium caprolactamate.

3. Cu-catalyzed cross-dehydrogenative coupling: a versatile strategy for C-C bond formations via the oxidative activation of sp(3) C-H bonds.

Review 4. Copper-Promoted Functionalization of Organic Molecules: from Biologically Relevant Cu/O₂ Model Systems to Organometallic Transformations.

5. Efficient domino approaches to multifunctionalized fused pyrroles and dibenzo[b,e][1,4]diazepin-1-ones.

6. Friedel-Crafts amidoalkylation via thermolysis and oxidative photocatalysis.

7. Brønsted acid cocatalysts in photocatalytic radical addition of α-amino C-H bonds across Michael acceptors.

8. Photoredox Activation and Anion Binding Catalysis in the Dual Catalytic Enantioselective Synthesis of β-Amino Esters.

9. Pd(OAc)(2)-catalyzed domino reactions of 1,2-dihaloarenes and 2-haloaryl arenesulfonates with Grignard reagents: efficient synthesis of substituted fluorenes.

10. α-Arylation of Saturated Azacycles and N-Methylamines via Palladium(II)-Catalyzed C(sp(3))-H Coupling.

Review 4. Copper-Promoted Functionalization of Organic Molecules: from Biologically Relevant Cu/O2 Model Systems to Organometallic Transformations.

Review 4. Copper-Promoted Functionalization of Organic Molecules: from Biologically Relevant Cu/O₂ Model Systems to Organometallic Transformations.