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Literature DB >> 18720970

Palladium-catalyzed carbonylation reactions of aryl bromides at atmospheric pressure: a general system based on Xantphos.

Joseph R Martinelli¹, Donald A Watson, Dominique M M Freckmann, Timothy E Barder, Stephen L Buchwald.

Abstract

A method for the Pd-catalyzed carbonylation of n class="Chemical">aryl bromides has been developed using Xantphos as the ligand. This method is effective for the direct synthesis of Weinreb amides, primary and secondary benzamides, and methyl esters from the corresponding aryl bromides at atmospheric pressure. In addition, a putative catalytic intermediate, (Xanphos)Pd(Br)benzoyl, was prepared and an X-ray crystal structure was obtained revealing an unusual cis-coordination mode of Xantphos in this palladium-acyl complex.

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Year: 2008 PMID： 18720970 PMCID： PMC2756424 DOI： 10.1021/jo801279r

Source DB: PubMed Journal: J Org Chem ISSN： 0022-3263 Impact factor: 4.354

22 in total

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2. Facile Ar-CF3 bond formation at Pd. Strikingly different outcomes of reductive elimination from [(Ph3P)2Pd(CF3)Ph] and [(Xantphos)Pd(CF3)Ph].

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Authors: Joseph R Martinelli; Thomas P Clark; Donald A Watson; Rachel H Munday; Stephen L Buchwald
Journal: Angew Chem Int Ed Engl Date: 2007 Impact factor: 15.336

4. Organometallic chemistry of amidate complexes. accelerating effect of bidentate ligands on the reductive elimination of N-aryl amidates from palladium(II).

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Authors:
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8. Carbonylative Sonogashira coupling of terminal alkynes with aqueous ammonia.

Authors: Mohamed S Mohammed Ahmed; Atsunori Mori
Journal: Org Lett Date: 2003-08-21 Impact factor: 6.005

9. Synthesis of Weinreb amides via Pd-catalyzed aminocarbonylation of heterocyclic-derived triflates.

Authors: A Deagostino; Paolo Larini; Ernesto G Occhiato; Lorena Pizzuto; Cristina Prandi; Paolo Venturello
Journal: J Org Chem Date: 2008-01-26 Impact factor: 4.354

10. Dimethylformamide as a carbon monoxide source in fast palladium-catalyzed aminocarbonylations of aryl bromides.

Authors: Yiqian Wan; Mathias Alterman; Mats Larhed; Anders Hallberg
Journal: J Org Chem Date: 2002-08-23 Impact factor: 4.354

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3. Efficient Synthesis of β-CF3/SCF3-Substituted Carbonyls via Copper-Catalyzed Electrophilic Ring-Opening Cross-Coupling of Cyclopropanols.

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4. Toward a rationale for the PTC124 (Ataluren) promoted readthrough of premature stop codons: a computational approach and GFP-reporter cell-based assay.

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5. Enantioselective Total Synthesis of Andrographolide and 14-Hydroxy-Colladonin: Carbonyl Reductive Coupling and trans-Decalin Formation by Hydrogen Transfer.

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Journal: Angew Chem Int Ed Engl Date: 2020-10-15 Impact factor: 15.336