Literature DB >> 19737014

Pd-catalyzed conversion of aryl chlorides, triflates, and nonaflates to nitroaromatics.

Brett P Fors1, Stephen L Buchwald.   

Abstract

An efficient Pd catalyst for the transformation of aryl chlorides, triflates, and nonaflates to nitroaromatics has been developed. This reaction proceeds under weakly basic conditions and displays a broad scope and excellent functional group compatibility. Moreover, this method allows for the synthesis of aromatic nitro compounds that cannot be accessed efficiently via other nitration protocols. Mechanistic insight into the transmetalation step of the catalytic process is also reported.

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Year:  2009        PMID: 19737014      PMCID: PMC2773681          DOI: 10.1021/ja905768k

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


  9 in total

1.  Effect of ligand steric properties and halide identity on the mechanism for oxidative addition of haloarenes to trialkylphosphine Pd(0) complexes.

Authors:  Fabiola Barrios-Landeros; Brad P Carrow; John F Hartwig
Journal:  J Am Chem Soc       Date:  2009-06-17       Impact factor: 15.419

Review 2.  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

3.  Aqueous hydroxide as a base for palladium-catalyzed amination of aryl chlorides and bromides.

Authors:  Ryoichi Kuwano; Masaru Utsunomiya; John F Hartwig
Journal:  J Org Chem       Date:  2002-09-06       Impact factor: 4.354

4.  Interaction of calcium channel antagonists with calcium: structural studies on nicardipine and its Ca2+ complex.

Authors:  M P Belciug; V S Ananthanarayanan
Journal:  J Med Chem       Date:  1994-12-09       Impact factor: 7.446

5.  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

6.  ipso-nitration of arylboronic acids with chlorotrimethylsilane-nitrate salts.

Authors:  G K Surya Prakash; Chiradeep Panja; Thomas Mathew; Vijayalakshmi Surampudi; Nicos A Petasis; George A Olah
Journal:  Org Lett       Date:  2004-06-24       Impact factor: 6.005

7.  A highly active catalyst for Pd-catalyzed amination reactions: cross-coupling reactions using aryl mesylates and the highly selective monoarylation of primary amines using aryl chlorides.

Authors:  Brett P Fors; Donald A Watson; Mark R Biscoe; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2008-09-18       Impact factor: 15.419

8.  Pd-catalyzed amidation of aryl chlorides using monodentate biaryl phosphine ligands: a kinetic, computational, and synthetic investigation.

Authors:  Takashi Ikawa; Timothy E Barder; Mark R Biscoe; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2007-10-05       Impact factor: 15.419

9.  Structure-dependent charge transport and storage in self-assembled monolayers of compounds of interest in molecular electronics: effects of tip material, headgroup, and surface concentration.

Authors:  Fu-Ren F Fan; Yuxing Yao; Lintao Cai; Long Cheng; James M Tour; Allen J Bard
Journal:  J Am Chem Soc       Date:  2004-03-31       Impact factor: 15.419

  9 in total
  23 in total

1.  Diamine Ligands in Copper-Catalyzed Reactions.

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

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

Authors:  David S Surry; Stephen L Buchwald
Journal:  Chem Sci       Date:  2011       Impact factor: 9.825

3.  A new biarylphosphine ligand for the Pd-catalyzed synthesis of diaryl ethers under mild conditions.

Authors:  Luca Salvi; Nicole R Davis; Siraj Z Ali; Stephen L Buchwald
Journal:  Org Lett       Date:  2011-12-19       Impact factor: 6.005

4.  A single phosphine ligand allows palladium-catalyzed intermolecular C-O bond formation with secondary and primary alcohols.

Authors:  Xiaoxing Wu; Brett P Fors; Stephen L Buchwald
Journal:  Angew Chem Int Ed Engl       Date:  2011-09-12       Impact factor: 15.336

5.  A novel route to organonitrites by Pd-catalyzed cross-coupling of sodium nitrite and potassium organotrifluoroborates.

Authors:  Mohammad Al-Masum; Nabil Saleh; Tasfia Islam
Journal:  Tetrahedron Lett       Date:  2013-02-01       Impact factor: 2.415

6.  Palladium-catalyzed cross-coupling of aryl chlorides and triflates with sodium cyanate: a practical synthesis of unsymmetrical ureas.

Authors:  Ekaterina V Vinogradova; Brett P Fors; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2012-06-29       Impact factor: 15.419

7.  Pd-catalyzed synthesis of Ar-SCF3 compounds under mild conditions.

Authors:  Georgiy Teverovskiy; David S Surry; Stephen L Buchwald
Journal:  Angew Chem Int Ed Engl       Date:  2011-06-20       Impact factor: 15.336

8.  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

9.  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

10.  Mild and highly selective palladium-catalyzed monoarylation of ammonia enabled by the use of bulky biarylphosphine ligands and palladacycle precatalysts.

Authors:  Chi Wai Cheung; David S Surry; Stephen L Buchwald
Journal:  Org Lett       Date:  2013-07-01       Impact factor: 6.005

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