Literature DB >> 25407817

The direct electrophilic cyanation of β-keto esters and amides with cyano benziodoxole.

Yao-Feng Wang1, Jiashen Qiu, Dejie Kong, Yongtao Gao, Feipeng Lu, Pran Gopal Karmaker, Fu-Xue Chen.   

Abstract

The direct electrophilic α-cyanation of β-keto esters and amides has been developed using a hypervalent iodine benziodoxole-derived cyano reagent. The procedure is accomplished within 10 min and without the use of any catalyst in DMF, at room temperature. Thus, the highly functionalized quaternary carbon-centered nitriles were produced in high to excellent yields.

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Year:  2014        PMID: 25407817     DOI: 10.1039/c4ob02032d

Source DB:  PubMed          Journal:  Org Biomol Chem        ISSN: 1477-0520            Impact factor:   3.876


  4 in total

Review 1.  Direct cyanation, hydrocyanation, dicyanation and cyanofunctionalization of alkynes.

Authors:  Lifen Peng; Zhifang Hu; Hong Wang; Li Wu; Yinchun Jiao; Zilong Tang; Xinhua Xu
Journal:  RSC Adv       Date:  2020-03-10       Impact factor: 4.036

2.  Towards an asymmetric organocatalytic α-cyanation of β-ketoesters.

Authors:  Raghunath Chowdhury; Johannes Schörgenhumer; Johanna Novacek; Mario Waser
Journal:  Tetrahedron Lett       Date:  2015-04-01       Impact factor: 2.415

3.  Room temperature decarboxylative cyanation of carboxylic acids using photoredox catalysis and cyanobenziodoxolones: a divergent mechanism compared to alkynylation.

Authors:  Franck Le Vaillant; Matthew D Wodrich; Jérôme Waser
Journal:  Chem Sci       Date:  2016-12-22       Impact factor: 9.825

4.  Preparation, structure, and reactivity of bicyclic benziodazole: a new hypervalent iodine heterocycle.

Authors:  Akira Yoshimura; Michael T Shea; Cody L Makitalo; Melissa E Jarvi; Gregory T Rohde; Akio Saito; Mekhman S Yusubov; Viktor V Zhdankin
Journal:  Beilstein J Org Chem       Date:  2018-05-08       Impact factor: 2.883

  4 in total

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