Literature DB >> 15040734

Copper-catalyzed coupling of imines, acid chlorides, and alkynes: a multicomponent route to propargylamides.

Daniel A Black1, Bruce A Arndtsen.   

Abstract

The use of imines in a metal-catalyzed coupling with alkynes and acid chlorides is described. This process proceeds rapidly with CuI as the catalyst and provides an efficient and general three-component coupling method to prepare propargylamides. The coupling can also be diversified to allow the formation of N-carbamate-protected propargylamines with the use of chloroformates.

Entities:  

Year:  2004        PMID： 15040734     DOI： 10.1021/ol036462+

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  12 in total

1.  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

2.  Synthesis of Diverse Heterocyclic Scaffolds via Tandem Additions to Imine Derivatives and Ring-Forming Reactions.

Authors:  James D Sunderhaus; Chris Dockendorff; Stephen F Martin
Journal:  Tetrahedron       Date:  2009-09-15       Impact factor: 2.457

3.  Silver(I) triflate-catalyzed direct synthesis of N-PMP protected alpha-aminopropargylphosphonates from terminal alkynes.

Authors:  Rajasekhar Dodda; Cong-Gui Zhao
Journal:  Org Lett       Date:  2007-01-04       Impact factor: 6.005

4.  Catalytic asymmetric alkynylation of alpha-imino ester: a versatile approach to optically active unnatural alpha-amino acid derivatives.

Authors:  Jian-Xin Ji; Jing Wu; Albert S C Chan
Journal:  Proc Natl Acad Sci U S A       Date:  2005-08-01       Impact factor: 11.205

5.  Enantioselective synthesis of alpha-aminopropargylphosphonates.

Authors:  Rajasekhar Dodda; Cong-Gui Zhao
Journal:  Tetrahedron Lett       Date:  2007-06-18       Impact factor: 2.415

6.  A One-Pot Selective Synthesis of N-Boc Protected Secondary Amines: Tandem Direct Reductive Amination/N-Boc Protection.

Authors:  Raghupathi Neelarapu; Pavel A Petukhov
Journal:  Tetrahedron       Date:  2012-06-22       Impact factor: 2.457

7.  Enantioselective, Copper-Catalyzed Alkynylation of Ketimines To Deliver Isoquinolines with α-Diaryl Tetrasubstituted Stereocenters.

Authors:  Srimoyee Dasgupta; Jixin Liu; Clarissa A Shoffler; Glenn P A Yap; Mary P Watson
Journal:  Org Lett       Date:  2016-11-16       Impact factor: 6.005

8.  Sequential Cu(I)/Pd(0)-catalyzed multicomponent coupling and annulation protocol for the synthesis of indenoisoquinolines.

Authors:  Thiruvellore Thatai Jayanth; Lei Zhang; Thomas S Johnson; Helena C Malinakova
Journal:  Org Lett       Date:  2009-02-19       Impact factor: 6.005

9.  A practical route to tertiary diarylmethylamides or -carbamates from imines, organozinc reagents and acyl chlorides or chloroformates.

Authors:  Erwan Le Gall; Antoine Pignon; Thierry Martens
Journal:  Beilstein J Org Chem       Date:  2011-07-20       Impact factor: 2.883

Review 10.  Enantioselective additions of copper acetylides to cyclic iminium and oxocarbenium ions.

Authors:  Jixin Liu; Srimoyee Dasgupta; Mary P Watson
Journal:  Beilstein J Org Chem       Date:  2015-12-22       Impact factor: 2.883
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