Literature DB >> 18543973

Pyrrole-2-carboxylic acid as a ligand for the Cu-catalyzed reactions of primary anilines with aryl halides.

Ryan A Altman1, Kevin W Anderson, Stephen L Buchwald.   

Abstract

Pyrrole 2-carboxylic acid (L5) was found to be an effective ligand for the Cu-catalyzed monoarylation of anilines with aryl iodides and bromides. Under the reported conditions (10% CuI/20% L5/DMSO/K3PO 4/80-100 degrees C/20-24 h), a variety of useful functional groups were tolerated, and moderate to good yields of the diaryl amine products were obtained.

Entities:  

Mesh:

Substances:

Year:  2008        PMID: 18543973      PMCID: PMC2582381          DOI: 10.1021/jo8008676

Source DB:  PubMed          Journal:  J Org Chem        ISSN: 0022-3263            Impact factor:   4.354


  17 in total

1.  The copper-catalyzed N-arylation of indoles.

Authors:  Jon C Antilla; Artis Klapars; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2002-10-02       Impact factor: 15.419

2.  Amino acid promoted CuI-catalyzed C-N bond formation between aryl halides and amines or N-containing heterocycles.

Authors:  Hui Zhang; Qian Cai; Dawei Ma
Journal:  J Org Chem       Date:  2005-06-24       Impact factor: 4.354

3.  N- versus O-arylation of aminoalcohols: orthogonal selectivity in copper-based catalysts.

Authors:  Alexandr Shafir; Phillip A Lichtor; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2007-03-07       Impact factor: 15.419

4.  Highly selective room-temperature copper-catalyzed C-N coupling reactions.

Authors:  Alexandr Shafir; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2006-07-12       Impact factor: 15.419

5.  Copper-catalyzed arylation of amines using diphenyl pyrrolidine-2-phosphonate as the new ligand.

Authors:  Honghua Rao; Hua Fu; Yuyang Jiang; Yufen Zhao
Journal:  J Org Chem       Date:  2005-09-30       Impact factor: 4.354

Review 6.  Biaryl phosphane ligands in palladium-catalyzed amination.

Authors:  David S Surry; Stephen L Buchwald
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

7.  Pd-catalyzed N-arylation of heteroarylamines.

Authors:  Jingjun Yin; Matthew M Zhao; Mark A Huffman; James M McNamara
Journal:  Org Lett       Date:  2002-10-03       Impact factor: 6.005

8.  Expanding Pd-catalyzed C-N bond-forming processes: the first amidation of aryl sulfonates, aqueous amination, and complementarity with Cu-catalyzed reactions.

Authors:  Xiaohua Huang; Kevin W Anderson; Danilo Zim; Lei Jiang; Artis Klapars; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2003-06-04       Impact factor: 15.419

9.  An improved Cu-based catalyst system for the reactions of alcohols with aryl halides.

Authors:  Ryan A Altman; Alexandr Shafir; Alice Choi; Phillip A Lichtor; Stephen L Buchwald
Journal:  J Org Chem       Date:  2007-11-29       Impact factor: 4.354

10.  Room-temperature copper-catalyzed alpha-arylation of malonates.

Authors:  Sau Fan Yip; Hong Yee Cheung; Zhongyuan Zhou; Fuk Yee Kwong
Journal:  Org Lett       Date:  2007-07-18       Impact factor: 6.005

View more
  5 in total

1.  Structurally Characterized Cationic Silver(I) and Ruthenium(II)carbene complexes of 1,2,3-Triazol-5-ylidenes.

Authors:  Jiajia Cai; Xiaoping Yang; Kuppuswamy Arumugam; Christopher W Bielawski; Jonathan L Sessler
Journal:  Organometallics       Date:  2011-09-26       Impact factor: 3.876

2.  Scalable total syntheses of N-linked tryptamine dimers by direct indole-aniline coupling: psychotrimine and kapakahines B and F.

Authors:  Timothy Newhouse; Chad A Lewis; Kyle J Eastman; Phil S Baran
Journal:  J Am Chem Soc       Date:  2010-05-26       Impact factor: 15.419

3.  Diamine Ligands in Copper-Catalyzed Reactions.

Authors:  David S Surry; Stephen L Buchwald
Journal:  Chem Sci       Date:  2010       Impact factor: 9.825

4.  Orthogonal Cu- and Pd-based catalyst systems for the O- and N-arylation of aminophenols.

Authors:  Debabrata Maiti; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2009-12-02       Impact factor: 15.419

5.  A room temperature copper catalyzed N-selective arylation of β-amino alcohols with iodoanilines and aryl iodides.

Authors:  Priyabrata Das; Jef K De Brabander
Journal:  Tetrahedron       Date:  2013-09-09       Impact factor: 2.457

  5 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.