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Literature DB >> 16774238

Palladium-catalyzed intramolecular cyanoamidation of alkynyl and alkenyl cyanoformamides.

Yusuke Kobayashi¹, Haruhi Kamisaki, Reiko Yanada, Yoshiji Takemoto.

Abstract

[reaction: see text] The five- to seven-membered alpha-alkylidene lactams were prepared in 45-99% yield by the palladium-catalyzed cyanoamidation of alkynyl cyanoformamides. The reaction proceeded exclusively in a 5-exo mode, giving the corresponding (Z)-alkenes as major products. The reaction was also applied to 1,1-disubstituted alkenes to afford oxindoles bearing a quaternary carbon center.

Entities: Chemical

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Year: 2006 PMID： 16774238 DOI： 10.1021/ol060733+

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

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Cited

13 in total

1. Palladium catalyzed intramolecular acylcyanation of alkenes using α-iminonitriles.

Authors: Naveen R Rondla; Jodi M Ogilvie; Zhongda Pan; Christopher J Douglas
Journal: Chem Commun (Camb) Date: 2014-08-18 Impact factor: 6.222

2. Diastereoselective Intramolecular Cyanoamidation with Alkenes.

Authors: Ashley M Dreis; Sadie C Otte; Matthew S Eastwood; Elizabeth R Alonzi; Jason T Brethorst; Christopher J Douglas
Journal: European J Org Chem Date: 2016-12-13

3. Studies towards the total synthesis of drimentine C. Preparation of the AB and CDEF ring fragments.

Authors: Sarah M Pound; Steven J Underwood; Christopher J Douglas
Journal: European J Org Chem Date: 2020-03-19

4. Mechanistic Model for Enantioselective Intramolecular Alkene Cyanoamidation via Palladium-Catalyzed C-CN Bond Activation.

Authors: Grant B Frost; Nicholas A Serratore; Jodi M Ogilvie; Christopher J Douglas
Journal: J Org Chem Date: 2017-03-15 Impact factor: 4.354

10. Rh-Catalyzed Decarbonylation of Conjugated Ynones via Carbon-Alkyne Bond Activation: Reaction Scope and Mechanistic Exploration via DFT Calculations.

Authors: Alpay Dermenci; Rachel E Whittaker; Yang Gao; Faben A Cruz; Zhi-Xiang Yu; Guangbin Dong
Journal: Chem Sci Date: 2015 Impact factor: 9.825

Palladium-catalyzed intramolecular cyanoamidation of alkynyl and alkenyl cyanoformamides.

1. Palladium catalyzed intramolecular acylcyanation of alkenes using α-iminonitriles.

2. Diastereoselective Intramolecular Cyanoamidation with Alkenes.

3. Studies towards the total synthesis of drimentine C. Preparation of the AB and CDEF ring fragments.

4. Mechanistic Model for Enantioselective Intramolecular Alkene Cyanoamidation via Palladium-Catalyzed C-CN Bond Activation.

5. Transition Metals Catalyzed Element-Cyano Bonds Activations.

6. Asymmetric intramolecular arylcyanation of unactivated olefins via C-CN bond activation.

7. "Cut and Sew" Transformations via Transition-Metal-Catalyzed Carbon-Carbon Bond Activation.

8. Transformations of X (C, O, N)-CN Bonds: Cases of Selective X (C, O, N)-C Activation.

9. Direct alkenylation of indolin-2-ones by 6-aryl-4-methylthio-2H-pyran-2-one-3-carbonitriles: a novel approach.

10. Rh-Catalyzed Decarbonylation of Conjugated Ynones via Carbon-Alkyne Bond Activation: Reaction Scope and Mechanistic Exploration via DFT Calculations.