A Lewis acid-promoted Pinner reaction

D Pfaff, G Nemecek, J Podlech

Index: Pfaff, Dominik; Nemecek, Gregor; Podlech, Joachim Beilstein Journal of Organic Chemistry, 2013 , vol. 9, p. 1572 - 1577

Full Text: HTML

Citation Number: 4

Abstract

Abstract Carbonitriles and alcohols react in a Lewis acid-promoted Pinner reaction to carboxylic esters. Best results are obtained with two equivalents of trimethylsilyl triflate as Lewis acid. Good yields are achieved with primary alcohols and aliphatic or benzylic carbonitriles, but the straightforward synthesis of acrylates and benzoates starting with acrylonitrile and benzonitrile, respectively, is similarly possible. Phenols are not acylated ...

~22%

~25%

~60%

~18%

~61%

~29%

~23%

~75%

~90%

~89%

~40%

~39%

~69%

~26%

~80%

~84%

A green protocol for chemoselective O-acylation in the prese...

[Tamaddon, Fatemeh; Amrollahi, Mohammad Ali; Sharafat, Leily Tetrahedron Letters, 2005 , vol. 46, # 45 p. 7841 - 7844]

A New Indirect Application of Aggregative Activation: Synthe...

[Marchal, Joel; Bodiguel, Jacques; Fort, Yves; Caubere, Paul Journal of Organic Chemistry, 1995 , vol. 60, # 26 p. 8336 - 8340]

Chemistry and Synthetic Utility of α-(Dimethylamino) benzyli...

[Wakita, Natsumi; Hara, Shoji Tetrahedron, 2010 , vol. 66, # 40 p. 7939 - 7945]

Cobalt (II)-catalyzed direct acetylation of alcohols with ac...

[Velusamy, Subbarayan; Borpuzari, Sarbani; Punniyamurthy Tetrahedron, 2005 , vol. 61, # 8 p. 2011 - 2015]

Chemistry and Synthetic Utility of α-(Dimethylamino) benzyli...

[Wakita, Natsumi; Hara, Shoji Tetrahedron, 2010 , vol. 66, # 40 p. 7939 - 7945]