Literature DB >> 19518153

Room-temperature Pd-catalyzed amidation of aryl bromides using tert-butyl carbamate.

Swapna Bhagwanth1, Alex G Waterson, George M Adjabeng, Keith R Hornberger.   

Abstract

The scope of Pd-catalyzed synthesis of N-Boc-protected anilines from aryl bromides and commercially available tert-butyl carbamate is described. For the first time, this process can be conducted at room temperature (17-22 degrees C) using a combination of Pd(2)dba(3).CHCl(3) and a monodentate ligand, tert-butyl X-Phos. Use of sodium tert-butoxide is crucial to the success of the reaction, which proceeds in 43-83% yield.

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Year:  2009        PMID: 19518153     DOI: 10.1021/jo9004537

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


  12 in total

1.  Dialkylbiaryl Phosphines in Pd-Catalyzed Amination: A User's Guide.

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2.  Palladium-catalyzed coupling of ammonia with aryl chlorides, bromides, iodides, and sulfonates: a general method for the preparation of primary arylamines.

Authors:  Giang D Vo; John F Hartwig
Journal:  J Am Chem Soc       Date:  2009-08-12       Impact factor: 15.419

3.  Synthesis and biological evaluation of orally active prodrugs and analogs of para-aminosalicylic acid (PAS).

Authors:  Pooja V Hegde; Michael D Howe; Matthew D Zimmerman; Helena I M Boshoff; Sachin Sharma; Brianna Remache; Ziyi Jia; Yan Pan; Anthony D Baughn; Veronique Dartois; Courtney C Aldrich
Journal:  Eur J Med Chem       Date:  2022-02-19       Impact factor: 6.514

4.  Pd-catalyzed N-arylation of secondary acyclic amides: catalyst development, scope, and computational study.

Authors:  Jacqueline D Hicks; Alan M Hyde; Alberto Martinez Cuezva; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2009-11-25       Impact factor: 15.419

5.  Investigating the dearomative rearrangement of biaryl phosphine-ligated Pd(II) complexes.

Authors:  Phillip J Milner; Thomas J Maimone; Mingjuan Su; Jiahao Chen; Peter Müller; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2012-11-27       Impact factor: 15.419

6.  Discovery of VU0431316: a negative allosteric modulator of mGlu5 with activity in a mouse model of anxiety.

Authors:  Brittney S Bates; Alice L Rodriguez; Andrew S Felts; Ryan D Morrison; Daryl F Venable; Anna L Blobaum; Frank W Byers; Kera P Lawson; J Scott Daniels; Colleen M Niswender; Carrie K Jones; P Jeffrey Conn; Craig W Lindsley; Kyle A Emmitte
Journal:  Bioorg Med Chem Lett       Date:  2014-06-11       Impact factor: 2.823

7.  Transitioning organic synthesis from organic solvents to water. What's your E Factor?

Authors:  Bruce H Lipshutz; Subir Ghorai
Journal:  Green Chem       Date:  2014-08-01       Impact factor: 10.182

8.  Installation of protected ammonia equivalents onto aromatic & heteroaromatic rings in water enabled by micellar catalysis.

Authors:  Nicholas A Isley; Sebastian Dobarco; Bruce H Lipshutz
Journal:  Green Chem       Date:  2014-01-02       Impact factor: 10.182

Review 9.  Applications of Palladium-Catalyzed C-N Cross-Coupling Reactions.

Authors:  Paula Ruiz-Castillo; Stephen L Buchwald
Journal:  Chem Rev       Date:  2016-09-30       Impact factor: 60.622

10.  Synthesis of rhodamines from fluoresceins using Pd-catalyzed C-N cross-coupling.

Authors:  Jonathan B Grimm; Luke D Lavis
Journal:  Org Lett       Date:  2011-11-17       Impact factor: 6.005

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