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Literature DB >> 16366529

Nickel-catalyzed cross-coupling reaction of aryl fluorides and chlorides with grignard reagents under nickel/magnesium bimetallic cooperation.

Naohiko Yoshikai¹, Hiroko Mashima, Eiichi Nakamura.

Abstract

Nickel-catalyzed cross-coupling of Grignard reagents with aryl (poly)fluorides or (poly)chlorides can be achieved efficiently in the presence of a new triarylphosphine ligand bearing a nearby hydroxy group. The high reactivity and the unique chemoselectivity (ArF > ArOTf > ArSR) of the catalysis have been attributed to synergy of nickel and magnesium atoms preorganized on the ligand, as has been surmised on the basis of theoretical modeling of the reaction mechanism.

Entities: Chemical

Year: 2005 PMID： 16366529 DOI： 10.1021/ja056327n

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

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Cited

14 in total

Review 1. Nickel-catalyzed cross-couplings involving carbon-oxygen bonds.

Authors: Brad M Rosen; Kyle W Quasdorf; Daniella A Wilson; Na Zhang; Ana-Maria Resmerita; Neil K Garg; Virgil Percec
Journal: Chem Rev Date: 2010-12-06 Impact factor: 60.622

2. Nickel-catalyzed amination of aryl sulfamates.

Authors: Stephen D Ramgren; Amanda L Silberstein; Yang Yang; Neil K Garg
Journal: Angew Chem Int Ed Engl Date: 2011-01-20 Impact factor: 15.336

3. Dual C-F, C-H Functionalization via Photocatalysis: Access to Multifluorinated Biaryls.

Authors: Sameera Senaweera; Jimmie D Weaver
Journal: J Am Chem Soc Date: 2016-02-18 Impact factor: 15.419

4. Suzuki-Miyaura cross-coupling of aryl carbamates and sulfamates: experimental and computational studies.

Authors: Kyle W Quasdorf; Aurora Antoft-Finch; Peng Liu; Amanda L Silberstein; Anna Komaromi; Tom Blackburn; Stephen D Ramgren; K N Houk; Victor Snieckus; Neil K Garg
Journal: J Am Chem Soc Date: 2011-04-01 Impact factor: 15.419

5. Asymmetric alkyl-alkyl cross-couplings of unactivated secondary alkyl electrophiles: stereoconvergent Suzuki reactions of racemic acylated halohydrins.

Authors: Nathan A Owston; Gregory C Fu
Journal: J Am Chem Soc Date: 2010-09-01 Impact factor: 15.419

Nickel-catalyzed cross-coupling reaction of aryl fluorides and chlorides with grignard reagents under nickel/magnesium bimetallic cooperation.

Review 1. Nickel-catalyzed cross-couplings involving carbon-oxygen bonds.

2. Nickel-catalyzed amination of aryl sulfamates.

3. Dual C-F, C-H Functionalization via Photocatalysis: Access to Multifluorinated Biaryls.

4. Suzuki-Miyaura cross-coupling of aryl carbamates and sulfamates: experimental and computational studies.

5. Asymmetric alkyl-alkyl cross-couplings of unactivated secondary alkyl electrophiles: stereoconvergent Suzuki reactions of racemic acylated halohydrins.

6. Photocatalytic C-F Reduction and Functionalization.

7. Suzuki-Miyaura coupling of aryl carbamates, carbonates, and sulfamates.

8. Aryl Fluoride Activation Through Palladium-Magnesium Bimetallic Cooperation: A Mechanistic and Computational Study.

9. Metal-metal cooperative bond activation by heterobimetallic alkyl, aryl, and acetylide Pt^II/Cu^I complexes.

10. General method for functionalized polyaryl synthesis via aryne intermediates.