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Literature DB >> 20857936

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

Xiaoqiang Shen¹, Alan M Hyde, Stephen L Buchwald.

Abstract

The palladium-catalyzed conversion of aryl and vinyl triflates to aryl and vinyl halides (bromides and chlorides) has been developed using dialkylbiaryl phosphine ligands. A variety of aryl, heteroaryl, and vinyl halides can be prepared via this method in good to excellent yields.

Entities: Chemical Gene

Mesh：

Substances：

Year: 2010 PMID： 20857936 PMCID： PMC2975586 DOI： 10.1021/ja107481a

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

24 in total

1. Reductive elimination of aryl halides from palladium(II).

Authors: A H Roy; J F Hartwig
Journal: J Am Chem Soc Date: 2001-02-14 Impact factor: 15.419

2. Aryl-halide versus aryl-aryl reductive elimination in Pt(IV)-phosphine complexes.

Authors: Anette Yahav-Levi; Israel Goldberg; Arkadi Vigalok
Journal: J Am Chem Soc Date: 2006-07-12 Impact factor: 15.419

3. Copper-catalyzed halogen exchange in aryl halides: an aromatic Finkelstein reaction.

Authors: Artis Klapars; Stephen L Buchwald
Journal: J Am Chem Soc Date: 2002-12-18 Impact factor: 15.419

4. The selective reaction of aryl halides with KOH: synthesis of phenols, aromatic ethers, and benzofurans.

Authors: Kevin W Anderson; Takashi Ikawa; Rachel E Tundel; Stephen L Buchwald
Journal: J Am Chem Soc Date: 2006-08-23 Impact factor: 15.419

5. 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

6. 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

Review 7. 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

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. Metal-mediated formation of carbon-halogen bonds.

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

10. Synthesis and reactivity of a mono-sigma-aryl palladium(IV) fluoride complex.

Authors: Nicholas D Ball; Melanie S Sanford
Journal: J Am Chem Soc Date: 2009-03-25 Impact factor: 15.419

19 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. C-H carbonylation: In situ acyl triflates ace it.

Authors: Yong Ho Lee; Bill Morandi
Journal: Nat Chem Date: 2018-01-23 Impact factor: 24.427

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

Authors: Jun Pan; Xinyan Wang; Yong Zhang; Stephen L Buchwald
Journal: Org Lett Date: 2011-08-24 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