Literature DB >> 22288653

Cross-coupling of non-activated chloroalkanes with aryl Grignard reagents in the presence of iron/N-heterocyclic carbene catalysts.

Sujit K Ghorai1, Masayoshi Jin, Takuji Hatakeyama, Masaharu Nakamura.   

Abstract

An efficient and high-yielding cross-coupling reaction of various primary, secondary, and tertiary alkyl chlorides with aryl Grignard reagents was achieved by using catalytic amounts of N-heterocyclic carbene ligands and iron salts. This reaction is a simple and efficient arylation method having applicability to a wide range of industrially abundant chloroalkanes, including polychloroalkanes, which are challenging substrates under conventional cross-coupling conditions.

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Year:  2012        PMID: 22288653     DOI: 10.1021/ol2031729

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


  17 in total

1.  A Physical-Inorganic Approach for the Elucidation of Active Iron Species and Mechanism in Iron-Catalyzed Cross-Coupling.

Authors:  Stephanie H Carpenter; Michael L Neidig
Journal:  Isr J Chem       Date:  2017-08-24       Impact factor: 3.333

2.  Combined Effects of Backbone and N-Substituents on Structure, Bonding, and Reactivity of Alkylated Iron(II)-NHCs.

Authors:  Salvador B Muñoz; Valerie E Fleischauer; William W Brennessel; Michael L Neidig
Journal:  Organometallics       Date:  2018-09-06       Impact factor: 3.876

3.  Iron-catalyzed cross-coupling of unactivated secondary alkyl thio ethers and sulfones with aryl Grignard reagents.

Authors:  Scott E Denmark; Alexander J Cresswell
Journal:  J Org Chem       Date:  2013-11-20       Impact factor: 4.354

4.  Additive and Counterion Effects in Iron-Catalyzed Reactions Relevant to C-C Bond Formation.

Authors:  Nikki J Bakas; Michael L Neidig
Journal:  ACS Catal       Date:  2021-06-29       Impact factor: 13.700

5.  Development and Evolution of Mechanistic Understanding in Iron-Catalyzed Cross-Coupling.

Authors:  Michael L Neidig; Stephanie H Carpenter; Daniel J Curran; Joshua C DeMuth; Valerie E Fleischauer; Theresa E Iannuzzi; Peter G N Neate; Jeffrey D Sears; Nikki J Wolford
Journal:  Acc Chem Res       Date:  2018-12-28       Impact factor: 22.384

6.  Ti-Catalyzed Radical Alkylation of Secondary and Tertiary Alkyl Chlorides Using Michael Acceptors.

Authors:  Xiangyu Wu; Wei Hao; Ke-Yin Ye; Binyang Jiang; Gisselle Pombar; Zhidong Song; Song Lin
Journal:  J Am Chem Soc       Date:  2018-10-26       Impact factor: 15.419

7.  Intermediates and Mechanism in Iron-Catalyzed Cross-Coupling.

Authors:  Jeffrey D Sears; Peter G N Neate; Michael L Neidig
Journal:  J Am Chem Soc       Date:  2018-09-18       Impact factor: 15.419

8.  C-Term magnetic circular dichroism (MCD) spectroscopy in paramagnetic transition metal and f-element organometallic chemistry.

Authors:  Nikki J Wolford; Aleksa Radovic; Michael L Neidig
Journal:  Dalton Trans       Date:  2020-12-14       Impact factor: 4.390

9.  A combined magnetic circular dichroism and density functional theory approach for the elucidation of electronic structure and bonding in three- and four-coordinate iron(II)-N-heterocyclic carbene complexes.

Authors:  Kathlyn L Fillman; Jacob A Przyojski; Malik H Al-Afyouni; Zachary J Tonzetich; Michael L Neidig
Journal:  Chem Sci       Date:  2015-02       Impact factor: 9.825

10.  NHC Effects on Reduction Dynamics in Iron-Catalyzed Organic Transformations*.

Authors:  Nikki J Wolford; Salvador B Muñoz; Peter G N Neate; William W Brennessel; Michael L Neidig
Journal:  Chemistry       Date:  2021-08-04       Impact factor: 5.020

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