Literature DB >> 21863838

An improved palladium-catalyzed conversion of aryl and vinyl triflates to bromides and chlorides.

Jun Pan1, Xinyan Wang, Yong Zhang, Stephen L Buchwald.   

Abstract

A facile Pd-catalyzed conversion of aryl and vinyl triflates to aryl and vinyl halides (bromides and chlorides) is described. This method allows convenient access to a variety of aryl, heteroaryl, and vinyl halides in good to excellent yields and with greatly simplified conditions relative to our previous report.
© 2011 American Chemical Society

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Year:  2011        PMID： 21863838      PMCID： PMC3170430          DOI： 10.1021/ol202098h

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


  14 in total

1.  Aryl-aryl bond formation one century after the discovery of the Ullmann reaction.

Authors:  Jwanro Hassan; Marc Sévignon; Christel Gozzi; Emmanuelle Schulz; Marc Lemaire
Journal:  Chem Rev       Date:  2002-05       Impact factor: 60.622

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.  The role of reversible oxidative addition in selective palladium(0)-catalyzed intramolecular cross-couplings of polyhalogenated substrates: synthesis of brominated indoles.

Authors:  Stephen G Newman; Mark Lautens
Journal:  J Am Chem Soc       Date:  2010-08-25       Impact factor: 15.419

4.  Efficient synthesis and structural characteristics of zwitterionic twisted pi-electron system biaryls.

Authors:  Hu Kang; Antonio Facchetti; Charlotte L Stern; Arnold L Rheingold; W Scott Kassel; Tobin J Marks
Journal:  Org Lett       Date:  2005-08-18       Impact factor: 6.005

5.  Palladium-catalyzed conversion of aryl and vinyl triflates to bromides and chlorides.

Authors:  Xiaoqiang Shen; Alan M Hyde; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2010-10-13       Impact factor: 15.419

Review 6.  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

Review 7.  The organometallic fluorine chemistry of palladium and rhodium: studies toward aromatic fluorination.

Authors:  Vladimir V Grushin
Journal:  Acc Chem Res       Date:  2010-01-19       Impact factor: 22.384

8.  Metal-catalysed halogen exchange reactions of aryl halides.

Authors:  Tom D Sheppard
Journal:  Org Biomol Chem       Date:  2009-01-30       Impact factor: 3.876

9.  Metal-mediated formation of carbon-halogen bonds.

Authors:  Arkadi Vigalok
Journal:  Chemistry       Date:  2008       Impact factor: 5.236

10.  Formation of ArF from LPdAr(F): catalytic conversion of aryl triflates to aryl fluorides.

Authors:  Donald A Watson; Mingjuan Su; Georgiy Teverovskiy; Yong Zhang; Jorge García-Fortanet; Tom Kinzel; Stephen L Buchwald
Journal:  Science       Date:  2009-08-13       Impact factor: 47.728
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  10 in total

1.  Total Synthesis of (-)-Nodulisporic Acids D, C, and B: Evolution of a Unified Synthetic Strategy.

Authors:  Yike Zou; Xiangqin Li; Yun Yang; Simon Berritt; Jason Melvin; Stephen Gonzales; Matthew Spafford; Amos B Smith
Journal:  J Am Chem Soc       Date:  2018-07-20       Impact factor: 15.419

2.  Stereoselective Synthesis of Trisubstituted Vinyl Bromides by Addition of Alkynes to Oxocarbenium Ions.

Authors:  Andrew R Ehle; Melissa G Morris; Bryan D Klebon; Glenn P A Yap; Mary P Watson
Journal:  Synlett       Date:  2015-09-14       Impact factor: 2.454

3.  Nickel-Catalyzed Conversion of Enol Triflates into Alkenyl Halides.

Authors:  Julie L Hofstra; Kelsey E Poremba; Alex M Shimozono; Sarah E Reisman
Journal:  Angew Chem Int Ed Engl       Date:  2019-09-19       Impact factor: 15.336

4.  Pd-Catalyzed Decarbonylative Cross-Couplings of Aroyl Chlorides.

Authors:  Christian A Malapit; Naoko Ichiishi; Melanie S Sanford
Journal:  Org Lett       Date:  2017-07-19       Impact factor: 6.005

5.  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

6.  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

7.  Organocatalytic, diastereo- and enantioselective synthesis of nonsymmetric cis-stilbene diamines: a platform for the preparation of single-enantiomer cis-imidazolines for protein-protein inhibition.

Authors:  Brandon A Vara; Anand Mayasundari; John C Tellis; Michael W Danneman; Vanessa Arredondo; Tyler A Davis; Jaeki Min; Kristin Finch; R Kiplin Guy; Jeffrey N Johnston
Journal:  J Org Chem       Date:  2014-07-14       Impact factor: 4.354

8.  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

9.  Pd-catalyzed nucleophilic fluorination of aryl bromides.

Authors:  Hong Geun Lee; Phillip J Milner; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2014-02-27       Impact factor: 15.419

10.  Nucleophile promoted gold redox catalysis with diazonium salts: C-Br, C-S and C-P bond formation through catalytic Sandmeyer coupling.

Authors:  Haihui Peng; Rong Cai; Chang Xu; Hao Chen; Xiaodong Shi
Journal:  Chem Sci       Date:  2016-06-10       Impact factor: 9.825
  10 in total

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