Literature DB >> 22612592

Nickel-catalyzed carboxylation of aryl and vinyl chlorides employing carbon dioxide.

Tetsuaki Fujihara1, Keisuke Nogi, Tinghua Xu, Jun Terao, Yasushi Tsuji.   

Abstract

Nickel-catalyzed carboxylation of aryl and vinyl chlorides employing carbon dioxide has been developed. The reactions proceeded under a CO(2) pressure of 1 atm at room temperature in the presence of nickel catalysts and Mn powder as a reducing agent. Various aryl chlorides could be converted to the corresponding carboxylic acid in good to high yields. Furthermore, vinyl chlorides were successfully carboxylated with CO(2). Mechanistic study suggests that Ni(I) species is involved in the catalytic cycle.

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Year:  2012        PMID: 22612592     DOI: 10.1021/ja303514b

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


  27 in total

1.  Synthesis of Tetrasubstituted Alkenes by Tandem Metallacycle Formation/Cross-Electrophile Coupling.

Authors:  Kirk W Shimkin; John Montgomery
Journal:  J Am Chem Soc       Date:  2018-05-31       Impact factor: 15.419

2.  Cross-Electrophile Coupling of Unactivated Alkyl Chlorides.

Authors:  Holt A Sakai; Wei Liu; Chi Chip Le; David W C MacMillan
Journal:  J Am Chem Soc       Date:  2020-06-26       Impact factor: 15.419

3.  Development of an Improved System for the Carboxylation of Aryl Halides through Mechanistic Studies.

Authors:  David J Charboneau; Gary W Brudvig; Nilay Hazari; Hannah M C Lant; Andrew K Saydjari
Journal:  ACS Catal       Date:  2019-03-14       Impact factor: 13.084

Review 4.  Homogeneous Organic Electron Donors in Nickel-Catalyzed Reductive Transformations.

Authors:  David J Charboneau; Nilay Hazari; Haotian Huang; Mycah R Uehling; Susan L Zultanski
Journal:  J Org Chem       Date:  2022-06-07       Impact factor: 4.198

5.  Copper-Catalyzed Carboxylation of Aryl Iodides with Carbon Dioxide.

Authors:  Hung Tran-Vu; Olafs Daugulis
Journal:  ACS Catal       Date:  2013-10-04       Impact factor: 13.084

6.  Nickel(I) Aryl Species: Synthesis, Properties, and Catalytic Activity.

Authors:  Megan Mohadjer Beromi; Gourab Banerjee; Gary W Brudvig; Nilay Hazari; Brandon Q Mercado
Journal:  ACS Catal       Date:  2018-02-13       Impact factor: 13.084

7.  Nickel-Catalyzed Cross-Electrophile Coupling of Aryl Chlorides with Primary Alkyl Chlorides.

Authors:  Seoyoung Kim; Matthew J Goldfogel; Michael M Gilbert; Daniel J Weix
Journal:  J Am Chem Soc       Date:  2020-05-21       Impact factor: 15.419

8.  Insertion of CO2 Mediated by a (Xantphos)NiI -Alkyl Species.

Authors:  Justin B Diccianni; Chunhua T Hu; Tianning Diao
Journal:  Angew Chem Int Ed Engl       Date:  2019-08-14       Impact factor: 15.336

9.  Regioselective Enzymatic β-Carboxylation of para-Hydroxy- styrene Derivatives Catalyzed by Phenolic Acid Decarboxylases.

Authors:  Christiane Wuensch; Tea Pavkov-Keller; Georg Steinkellner; Johannes Gross; Michael Fuchs; Altijana Hromic; Andrzej Lyskowski; Kerstin Fauland; Karl Gruber; Silvia M Glueck; Kurt Faber
Journal:  Adv Synth Catal       Date:  2015-04-02       Impact factor: 5.837

10.  Stoichiometric Reactions of Acylnickel(II) Complexes with Electrophiles and the Catalytic Synthesis of Ketones.

Authors:  Alexander C Wotal; Ryan D Ribson; Daniel J Weix
Journal:  Organometallics       Date:  2014-07-10       Impact factor: 3.876

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