O-Iodoxybenzoic acid-and tetraethylammonium bromide-mediated oxidative transformation of primary carboxamides to one-carbon dehomologated nitriles

DS Bhalerao, US Mahajan, KH Chaudhari…

Index: Bhalerao, Dinesh S.; Mahajan, Ulhas S.; Chaudhari, Kiran H.; Akamanchi, Krishnacharya G. Journal of Organic Chemistry, 2007 , vol. 72, # 2 p. 662 - 665

Full Text: HTML

Citation Number: 46

Abstract

A clean and efficient method for the oxidative transformations of primary carboxamides to one-carbon dehomologated nitriles using the combination of o-iodoxybenzoic acid and tetraethylammonium bromide has been developed. This method exhibits a broad scope and is expected to be of great utility in organic synthesis.

~80%

~85%

~56%

~80%

~93%

~95%

~91%

~80%

~80%

~72%

~80%

~60%

~79%

Phosphonium salt-catalysed synthesis of nitriles from in sit...

[Denton, Ross M.; An, Jie; Lindovska, Petra; Lewis, William Tetrahedron, 2012 , vol. 68, # 13 p. 2899 - 2905]

Reactions of trimethylsilyl azide with aldehydes: facile and...

[Nishiyama, Kozaburo; Oba, Makoto; Watanabe, Akio Tetrahedron, 1987 , vol. 43, # 4 p. 693 - 700]

Oxidative fragmentation of oxiranes to nitriles with hyperva...

[Deshmukh, Swapnil S.; Huddar, Sameerana N.; Jadhav, Ravindra R.; Akamanchi, Krishnacharya G. Tetrahedron Letters, 2011 , vol. 52, # 35 p. 4533 - 4536]

Facile transformation of esters to nitriles

[Suzuki, Yusuke; Moriyama, Katsuhiko; Togo, Hideo Tetrahedron, 2011 , vol. 67, # 41 p. 7956 - 7962]

Practical one-pot conversion of aryl bromides and β-bromosty...

[Ishii, Genki; Harigae, Ryo; Moriyama, Katsuhiko; Togo, Hideo Tetrahedron, 2013 , vol. 69, # 5 p. 1462 - 1469]