Literature DB >> 24088068

Palladium-catalyzed fluorocarbonylation using N-formylsaccharin as CO source: general access to carboxylic acid derivatives.

Tsuyoshi Ueda1, Hideyuki Konishi, Kei Manabe.   

Abstract

N-formylsaccharin, an easily accessible crystalline compound, has been employed as an efficient CO source in Pd-catalyzed fluorocarbonylation of aryl halides to afford the corresponding acyl fluorides in high yields. The reactions use a near-stoichiometric amount of the CO source (1.2 equiv) and tolerate diverse functional groups. The acyl fluorides obtained could be readily transformed into various carboxylic acid derivatives such as carboxylic acid, esters, thioesters, and amides in a one-pot procedure.

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Year:  2013        PMID: 24088068     DOI: 10.1021/ol4026815

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


  10 in total

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Authors:  Peter C Ray; Margaret Huggett; Penelope A Turner; Malcolm Taylor; Laura A T Cleghorn; Julie Early; Anuradha Kumar; Shilah A Bonnett; Lindsay Flint; Douglas Joerss; James Johnson; Aaron Korkegian; Steven Mullen; Abraham L Moure; Susan H Davis; Dinakaran Murugesan; Michael Mathieson; Nicola Caldwell; Curtis A Engelhart; Dirk Schnappinger; Ola Epemolu; Fabio Zuccotto; Jennifer Riley; Paul Scullion; Laste Stojanovski; Lisa Massoudi; Gregory T Robertson; Anne J Lenaerts; Gail Freiberg; Dale J Kempf; Thierry Masquelin; Philip A Hipskind; Joshua Odingo; Kevin D Read; Simon R Green; Paul G Wyatt; Tanya Parish
Journal:  ACS Omega       Date:  2021-01-13

2.  Catalytic acceptorless dehydrogenations: Ru-Macho catalyzed construction of amides and imines.

Authors:  Nathan J Oldenhuis; Vy M Dong; Zhibin Guan
Journal:  Tetrahedron       Date:  2014-07-08       Impact factor: 2.457

3.  Nickel-catalyzed dehydrogenative cross-coupling: direct transformation of aldehydes into esters and amides.

Authors:  Aaron M Whittaker; Vy M Dong
Journal:  Angew Chem Int Ed Engl       Date:  2014-11-25       Impact factor: 15.336

4.  Synthesis of Complex Diterpenes: Strategies Guided by Oxidation Pattern Analysis.

Authors:  Sara E Dibrell; Yujia Tao; Sarah E Reisman
Journal:  Acc Chem Res       Date:  2021-02-23       Impact factor: 24.466

5.  A 16-step synthesis of the isoryanodane diterpene (+)-perseanol.

Authors:  Arthur Han; Yujia Tao; Sarah E Reisman
Journal:  Nature       Date:  2019-09-25       Impact factor: 49.962

6.  Enhancing stability by trapping palladium inside N-heterocyclic carbene-functionalized hypercrosslinked polymers for heterogeneous C-C bond formations.

Authors:  Chengtao Yue; Qi Xing; Peng Sun; Zelun Zhao; Hui Lv; Fuwei Li
Journal:  Nat Commun       Date:  2021-03-25       Impact factor: 14.919

Review 7.  Artificial sugar saccharin and its derivatives: role as a catalyst.

Authors:  Kamalpreet Kaur; Suman Srivastava
Journal:  RSC Adv       Date:  2020-10-06       Impact factor: 4.036

8.  5-Bromo-norborn-2-en-7-one derivatives as a carbon monoxide source for palladium catalyzed carbonylation reactions.

Authors:  China M Payne; Kyulee Cho; David S Larsen
Journal:  RSC Adv       Date:  2019-09-30       Impact factor: 4.036

9.  Palladium catalyzed synthesis of indolizines via the carbonylative coupling of bromopyridines, imines and alkynes.

Authors:  Sébastien A Roy; José Zgheib; Cuihan Zhou; Bruce A Arndtsen
Journal:  Chem Sci       Date:  2020-12-22       Impact factor: 9.825

10.  A flexible approach to Pd-catalyzed carbonylations via aroyl dimethylaminopyridinium salts.

Authors:  Jeffrey S Quesnel; Alexander Fabrikant; Bruce A Arndtsen
Journal:  Chem Sci       Date:  2015-09-30       Impact factor: 9.825

  10 in total

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