Literature DB >> 21604792

Synthesis of unsymmetrical diarylureas via Pd-catalyzed C-N cross-coupling reactions.

Simon Breitler1, Nathan J Oldenhuis, Brett P Fors, Stephen L Buchwald.   

Abstract

A facile synthesis of unsymmetrical N,N'-diarylureas is described. The utilization of the Pd-catalyzed arylation of ureas enables the synthesis of an array of diarylureas in good to excellent yields from benzylurea via a one-pot arylation-deprotection protocol, followed by a second arylation.
© 2011 American Chemical Society

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Year:  2011        PMID： 21604792      PMCID： PMC3127456          DOI： 10.1021/ol201210t

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


  19 in total

1.  Synthesis of a TRPV1 receptor antagonist.

Authors:  Su Yu; Anthony Haight; Brian Kotecki; Lei Wang; Kirill Lukin; David R Hill
Journal:  J Org Chem       Date:  2009-12-18       Impact factor: 4.354

2.  Efficient access to cyclic ureas via Pd-catalyzed cyclization.

Authors:  Mark McLaughlin; Michael Palucki; Ian W Davies
Journal:  Org Lett       Date:  2006-07-20       Impact factor: 6.005

3.  Practical synthesis of unsymmetrical ureas from isopropenyl carbamates.

Authors:  Isabelle Gallou; Magnus Eriksson; Xingzhong Zeng; Chris Senanayake; Vittorio Farina
Journal:  J Org Chem       Date:  2005-08-19       Impact factor: 4.354

4.  Discovery of omecamtiv mecarbil the first, selective, small molecule activator of cardiac Myosin.

Authors:  Bradley P Morgan; Alexander Muci; Pu-Ping Lu; Xiangping Qian; Todd Tochimoto; Whitney W Smith; Marc Garard; Erica Kraynack; Scott Collibee; Ion Suehiro; Adam Tomasi; S Corey Valdez; Wenyue Wang; Hong Jiang; James Hartman; Hector M Rodriguez; Raja Kawas; Sheila Sylvester; Kathleen A Elias; Guillermo Godinez; Kenneth Lee; Robert Anderson; Sandra Sueoka; Donghong Xu; Zhengping Wang; Nebojsa Djordjevic; Fady I Malik; David J Morgans
Journal:  ACS Med Chem Lett       Date:  2010-08-20       Impact factor: 4.345

5.  Synthesis of carbamates and ureas using Zr(IV)-catalyzed exchange processes.

Authors:  Chong Han; John A Porco
Journal:  Org Lett       Date:  2007-03-15       Impact factor: 6.005

6.  Evaluation of Diarylureas for Activity Against Plasmodium falciparum.

Authors:  Yiqun Zhang; Marc Anderson; Jennifer L Weisman; Min Lu; Cindy J Choy; Vincent A Boyd; Jeanine Price; Martina Sigal; Julie Clark; Michele Connelly; Fangyi Zhu; W Armand Guiguemde; Cynthia Jeffries; Lei Yang; Andrew Lemoff; Ally P Liou; Thomas R Webb; Joseph L Derisi; R Kiplin Guy
Journal:  ACS Med Chem Lett       Date:  2010-12-09       Impact factor: 4.345

7.  A general method for the synthesis of unsymmetrically substituted ureas via palladium-catalyzed amidation.

Authors:  Brian J Kotecki; Dilinie P Fernando; Anthony R Haight; Kirill A Lukin
Journal:  Org Lett       Date:  2009-02-19       Impact factor: 6.005

8.  Carbonyldiimidazole-mediated Lossen rearrangement.

Authors:  Pascal Dubé; Noah F Fine Nathel; Michael Vetelino; Michel Couturier; Claude Larrivée Aboussafy; Simon Pichette; Matthew L Jorgensen; Mark Hardink
Journal:  Org Lett       Date:  2009-12-17       Impact factor: 6.005

9.  An Efficient System For the Pd-Catalyzed Cross-Coupling of Amides and Aryl Chlorides.

Authors:  Brett P Fors; Karin Dooleweerdt; Qingle Zeng; Stephen L Buchwald
Journal:  Tetrahedron       Date:  2009-08-15       Impact factor: 2.457

10.  Unsymmetrical non-adamantyl N,N'-diaryl urea and amide inhibitors of soluble expoxide hydrolase.

Authors:  Sampath-Kumar Anandan; Heather K Webb; Zung N Do; Richard D Gless
Journal:  Bioorg Med Chem Lett       Date:  2009-05-30       Impact factor: 2.823
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  7 in total

1.  Evidence for in situ catalyst modification during the Pd-catalyzed conversion of aryl triflates to aryl fluorides.

Authors:  Thomas J Maimone; Phillip J Milner; Tom Kinzel; Yong Zhang; Michael K Takase; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2011-10-21       Impact factor: 15.419

2.  A practically simple, catalyst free and scalable synthesis of N-substituted ureas in water.

Authors:  Lata Tiwari; Varun Kumar; Bhuvesh Kumar; Dinesh Mahajan
Journal:  RSC Adv       Date:  2018-06-13       Impact factor: 4.036

3.  An Improved Synthesis of BrettPhos and RockPhos-Type Biarylphosphine Ligands.

Authors:  Naoyuki Hoshiya; Stephen L Buchwald
Journal:  Adv Synth Catal       Date:  2012-06-27       Impact factor: 5.837

4.  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

Review 5.  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

6.  Biaryl Monophosphine Ligands in Palladium-Catalyzed C-N Coupling: An Updated User's Guide.

Authors:  Bryan T Ingoglia; Corin C Wagen; Stephen L Buchwald
Journal:  Tetrahedron       Date:  2019-05-11       Impact factor: 2.457

7.  Regioselective synthesis of benzimidazolones via cascade C-N coupling of monosubstituted ureas.

Authors:  Johannes B Ernst; Nicholas E S Tay; Nathan T Jui; Stephen L Buchwald
Journal:  Org Lett       Date:  2014-06-27       Impact factor: 6.005
  7 in total

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