Literature DB >> 12643691

Catalytic transamidation under moderate conditions.

Sarah E Eldred1, David A Stone, Samuel H Gellman, Shannon S Stahl.   

Abstract

The carboxamide group is generally inert, except under harsh conditions or in the presence of highly evolved enzymes. We have identified several metal complexes that efficiently catalyze transamidation reactions of amide/amine mixtures under moderate conditions. This unprecedented reactivity represents an important step toward our long-term goal of using dynamic combinatorial chemistry to generate new amide-based molecules with interesting structures and functions.

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Year:  2003        PMID: 12643691     DOI: 10.1021/ja028242h

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


  12 in total

1.  Nucleophilic carbene and HOAt relay catalysis in an amide bond coupling: an orthogonal peptide bond forming reaction.

Authors:  Harit U Vora; Tomislav Rovis
Journal:  J Am Chem Soc       Date:  2007-10-11       Impact factor: 15.419

2.  Enantioselective photocycloaddition of 3-hydroxyflavones: total syntheses and absolute configuration assignments of (+)-ponapensin and (+)-elliptifoline.

Authors:  Neil J Lajkiewicz; Stéphane P Roche; Baudouin Gerard; John A Porco
Journal:  J Am Chem Soc       Date:  2012-07-25       Impact factor: 15.419

3.  Breaking Amides using Nickel Catalysis.

Authors:  Jacob E Dander; Neil K Garg
Journal:  ACS Catal       Date:  2017-01-06       Impact factor: 13.084

4.  Catalytic ester-amide exchange using group (IV) metal alkoxide-activator complexes.

Authors:  Chong Han; Jonathan P Lee; Emil Lobkovsky; John A Porco
Journal:  J Am Chem Soc       Date:  2005-07-20       Impact factor: 15.419

5.  Synthetic and Mechanistic Studies of Strained Heterocycle Opening Reactions Mediated by Zirconium(IV) Imido Complexes.

Authors:  Suzanne A Blum; Vicki A Rivera; Rebecca T Ruck; Forrest E Michael; Robert G Bergman
Journal:  Organometallics       Date:  2005-03-28       Impact factor: 3.876

6.  Water-Based Dynamic Depsipeptide Chemistry: Building Block Recycling and Oligomer Distribution Control Using Hydration-Dehydration Cycles.

Authors:  Martin C; Moran Frenkel-Pinter; Kelvin H Smith; Victor F Rivera-Santana; Alyssa B Sargon; Kaitlin C Jacobson; Aikomari Guzman-Martinez; Loren Dean Williams; Luke J Leman; Charles L Liotta; Martha A Grover; Nicholas V Hud
Journal:  JACS Au       Date:  2022-05-17

7.  meso-Tetra(pentafluorophenyl)porphyrin as an efficient platform for combinatorial synthesis and the selection of new photodynamic therapeutics using a cancer cell line.

Authors:  Diana Samaroo; Mikki Vinodu; Xin Chen; Charles Michael Drain
Journal:  J Comb Chem       Date:  2007-09-15

8.  Applications of C-H functionalization logic to cyclobutane synthesis.

Authors:  Will R Gutekunst; Phil S Baran
Journal:  J Org Chem       Date:  2014-02-27       Impact factor: 4.354

9.  A two-step approach to achieve secondary amide transamidation enabled by nickel catalysis.

Authors:  Emma L Baker; Michael M Yamano; Yujing Zhou; Sarah M Anthony; Neil K Garg
Journal:  Nat Commun       Date:  2016-05-20       Impact factor: 14.919

Review 10.  Recent advances in copper-catalyzed C-H bond amidation.

Authors:  Jie-Ping Wan; Yanfeng Jing
Journal:  Beilstein J Org Chem       Date:  2015-11-17       Impact factor: 2.883

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