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Literature DB >> 21644568

Nickel(0)-catalyzed cyclization of N-benzoylaminals for isoindolinone synthesis.

Danielle M Shacklady-McAtee¹, Srimoyee Dasgupta, Mary P Watson.

Abstract

A nickel(0) catalyst effectively mediates the cyclization of N-benzoyl aminals in the presence of a stoichiometric Lewis acid. This method enables preparation of a variety of isoindolinones with substitution on the benzoyl fragment and C-3 carbon. This reaction likely proceeds via an α-amidoalkylnickel(II) intermediate, which then may cyclize via either an electrophilic aromatic substitution or an insertion pathway.

Entities: Chemical Gene

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Year: 2011 PMID： 21644568 DOI： 10.1021/ol201248c

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

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Cited

7 in total

1. Tandem C(sp³)-H Arylation/Oxidation and Arylation/Allylic Substitution of Isoindolinones.

Authors: Jacqueline Jiménez; Byeong-Seon Kim; Patrick J Walsh
Journal: Adv Synth Catal Date: 2016-08-02 Impact factor: 5.837

2. Mechanistic investigation of the nickel-catalyzed Suzuki reaction of N,O-acetals: evidence for boronic acid assisted oxidative addition and an iminium activation pathway.

Authors: Kevin T Sylvester; Kevin Wu; Abigail G Doyle
Journal: J Am Chem Soc Date: 2012-10-05 Impact factor: 15.419

Nickel(0)-catalyzed cyclization of N-benzoylaminals for isoindolinone synthesis.

1. Tandem C(sp³)-H Arylation/Oxidation and Arylation/Allylic Substitution of Isoindolinones.

2. Mechanistic investigation of the nickel-catalyzed Suzuki reaction of N,O-acetals: evidence for boronic acid assisted oxidative addition and an iminium activation pathway.

3. Rhodium catalyzed synthesis of isoindolinones via C-H activation of N-benzoylsulfonamides.

4. Nickel-catalyzed enantioselective arylation of pyridinium ions: harnessing an iminium ion activation mode.

5. Highly Regioselective Synthesis of Substituted Isoindolinones via Ruthenium-Catalyzed Alkyne Cyclotrimerizations.

6. Nickel-catalyzed C-H/N-H annulation of aromatic amides with alkynes in the absence of a specific chelation system.

Review 7. Isoindolinone Synthesis via One-Pot Type Transition Metal Catalyzed C-C Bond Forming Reactions.

Nickel(0)-catalyzed cyclization of N-benzoylaminals for isoindolinone synthesis.

1. Tandem C(sp3)-H Arylation/Oxidation and Arylation/Allylic Substitution of Isoindolinones.

2. Mechanistic investigation of the nickel-catalyzed Suzuki reaction of N,O-acetals: evidence for boronic acid assisted oxidative addition and an iminium activation pathway.

3. Rhodium catalyzed synthesis of isoindolinones via C-H activation of N-benzoylsulfonamides.

4. Nickel-catalyzed enantioselective arylation of pyridinium ions: harnessing an iminium ion activation mode.

5. Highly Regioselective Synthesis of Substituted Isoindolinones via Ruthenium-Catalyzed Alkyne Cyclotrimerizations.

6. Nickel-catalyzed C-H/N-H annulation of aromatic amides with alkynes in the absence of a specific chelation system.

Review 7. Isoindolinone Synthesis via One-Pot Type Transition Metal Catalyzed C-C Bond Forming Reactions.

1. Tandem C(sp³)-H Arylation/Oxidation and Arylation/Allylic Substitution of Isoindolinones.