Literature DB >> 21804786

Aminations of Aryl Bromides in Water at Room Temperature.

Bruce H Lipshutz1, David W Chung, Brian Rich.   

Abstract

Unsymmetrical di- and triarylamines can be formed under green chemistry conditions, taking advantage of micellar catalysis leading to palladium-catalyzed aminations at ambient temperatures in water as the only medium.

Entities:  

Year:  2009        PMID： 21804786      PMCID： PMC3146389          DOI： 10.1002/adsc.200900323

Source DB:  PubMed          Journal:  Adv Synth Catal        ISSN： 1615-4150            Impact factor:   5.837


  16 in total

1.  Reactions in micellar systems.

Authors:  Torsten Dwars; Eckhard Paetzold; Günther Oehme
Journal:  Angew Chem Int Ed Engl       Date:  2005-11-11       Impact factor: 15.336

2.  Heck couplings at room temperature in nanometer aqueous micelles.

Authors:  Bruce H Lipshutz; Benjamin R Taft
Journal:  Org Lett       Date:  2008-03-12       Impact factor: 6.005

3.  Sonogashira couplings of aryl bromides: room temperature, water only, no copper.

Authors:  Bruce H Lipshutz; David W Chung; Brian Rich
Journal:  Org Lett       Date:  2008-08-07       Impact factor: 6.005

4.  Simple, efficient catalyst system for the palladium-catalyzed amination of aryl chlorides, bromides, and triflates.

Authors:  J P Wolfe; H Tomori; J P Sadighi; J Yin; S L Buchwald
Journal:  J Org Chem       Date:  2000-02-25       Impact factor: 4.354

Review 5.  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

6.  Evolution of a fourth generation catalyst for the amination and thioetherification of aryl halides.

Authors:  John F Hartwig
Journal:  Acc Chem Res       Date:  2008-11-18       Impact factor: 22.384

7.  Highly reactive, general and long-lived catalysts for palladium-catalyzed amination of heteroaryl and aryl chlorides, bromides, and iodides: scope and structure-activity relationships.

Authors:  Qilong Shen; Tokutaro Ogata; John F Hartwig
Journal:  J Am Chem Soc       Date:  2008-04-30       Impact factor: 15.419

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.  Modified (NHC)Pd(allyl)Cl (NHC = N-heterocyclic carbene) complexes for room-temperature Suzuki-Miyaura and Buchwald-Hartwig reactions.

Authors:  Nicolas Marion; Oscar Navarro; Jianguo Mei; Edwin D Stevens; Natalie M Scott; Steven P Nolan
Journal:  J Am Chem Soc       Date:  2006-03-29       Impact factor: 15.419

10.  Pd-catalyzed aryl amination mediated by well defined, N-heterocyclic carbene (NHC)-Pd precatalysts, PEPPSI.

Authors:  Michael G Organ; Mirvat Abdel-Hadi; Stephanie Avola; Igor Dubovyk; Niloufar Hadei; Eric Assen B Kantchev; Christopher J O'Brien; Mahmoud Sayah; Cory Valente
Journal:  Chemistry       Date:  2008       Impact factor: 5.236
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  12 in total

1.  "Designer"-Surfactant-Enabled Cross-Couplings in Water at Room Temperature.

Authors:  Bruce H Lipshutz; Subir Ghorai
Journal:  Aldrichimica Acta       Date:  2012-01-01       Impact factor: 3.667

2.  Synthesis and biological evaluation of arylated novobiocin analogs as Hsp90 inhibitors.

Authors:  Bhaskar Reddy Kusuma; Adam S Duerfeldt; Brian S J Blagg
Journal:  Bioorg Med Chem Lett       Date:  2011-10-01       Impact factor: 2.823

3.  "Nok": a phytosterol-based amphiphile enabling transition-metal-catalyzed couplings in water at room temperature.

Authors:  Piyatida Klumphu; Bruce H Lipshutz
Journal:  J Org Chem       Date:  2014-01-21       Impact factor: 4.354

4.  TPGS-750-M: a second-generation amphiphile for metal-catalyzed cross-couplings in water at room temperature.

Authors:  Bruce H Lipshutz; Subir Ghorai; Alexander R Abela; Ralph Moser; Takashi Nishikata; Christophe Duplais; Arkady Krasovskiy; Ricky D Gaston; Robert C Gadwood
Journal:  J Org Chem       Date:  2011-05-09       Impact factor: 4.354

Review 5.  Replacement of Less-Preferred Dipolar Aprotic and Ethereal Solvents in Synthetic Organic Chemistry with More Sustainable Alternatives.

Authors:  Andrew Jordan; Callum G J Hall; Lee R Thorp; Helen F Sneddon
Journal:  Chem Rev       Date:  2022-02-24       Impact factor: 72.087

6.  Amination of allylic alcohols in water at room temperature.

Authors:  Takashi Nishikata; Bruce H Lipshutz
Journal:  Org Lett       Date:  2009-06-04       Impact factor: 6.005

7.  Aminations of allylic phenyl ethers via micellar catalysis at room temperature in water.

Authors:  Takashi Nishikata; Bruce H Lipshutz
Journal:  Chem Commun (Camb)       Date:  2009-09-08       Impact factor: 6.222

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

9.  Aryl Amination Using Soluble Weak Base Enabled by a Water-Assisted Mechanism.

Authors:  Sii Hong Lau; Peng Yu; Liye Chen; Christina B Madsen-Duggan; Michael J Williams; Brad P Carrow
Journal:  J Am Chem Soc       Date:  2020-11-12       Impact factor: 15.419

10.  Sustainable ppm level palladium-catalyzed aminations in nanoreactors under mild, aqueous conditions.

Authors:  Yitao Zhang; Balaram S Takale; Fabrice Gallou; John Reilly; Bruce H Lipshutz
Journal:  Chem Sci       Date:  2019-09-20       Impact factor: 9.825
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