33268-94-9Relevant academic research and scientific papers
Tris(pentafluorophenyl)borane-Catalyzed Formal Cyanoalkylation of Indoles with Cyanohydrins
Kiyokawa, Kensuke,Minakata, Satoshi,Urashima, Naruyo
, p. 8389 - 8401 (2021/06/28)
Despite the significant achievements related to the C3 functionalization of indoles, cyanoalkylation reactions continue to remain rather limited. We herein report on the formal C3 cyanoalkylation of indoles with cyanohydrins in the presence of a tris(pentafluorophenyl)borane (B(C6F5)3) catalyst. It is noteworthy that cyanohydrins are used as a cyanoalkylating reagent in the present reaction, even though they are usually used as only a HCN source. Mechanistic investigations revealed the unique reactivity of the B(C6F5)3 catalyst in promoting the decomposition of a cyanohydrin by a Lewis acidic activation through the coordination of the cyano group to the boron center. In addition, a catalytic three-component reaction using indoles, aldehydes as a carbon unit, and acetone cyanohydrin that avoids the discrete preparation of each aldehyde-derived cyanohydrin is also reported. The developed methods provide straightforward, highly efficient, and atom-economic access to various types of synthetically useful indole-3-acetonitrile derivatives containing α-tertiary or quaternary carbon centers.
Gold-catalyzed oxidative couplings of two indoles with one aryldiazo cyanide under oxidant-free conditions
Singh, Rahulkumar Rajmani,Liu, Rai-Shung
, p. 4593 - 4596 (2017/04/28)
Gold-catalyzed oxidative couplings of two indoles and one α-cyano gold carbene to form bis(indolyl)methane derivatives are described. Two different indoles are compatible with these reactions to provide reasonable yields. A plausible mechanism is postulated to rationalize the experimental data including product distributions, D2O labeling, and the significant effects of gold catalysts and cyano groups.
Direct transformation of primary nitro compounds into nitriles with sodium-dithionite
Temelli, Baris,Unaleroglu, Canan
, p. 1407 - 1412 (2014/06/09)
A new and practical direct transformation of primary nitro compounds into nitriles with sodium dithionite is described. The reaction is simple, convenient and eliminates the use of expensive and moisture-sensitive reagents. Georg Thieme Verlag Stuttgart New York.
