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A Sterically Congested α‐Cyanoamine as a Cyanating Reagent: Cyanation of Acetals and Orthoesters
Author(s) -
Kotani Shunsuke,
Sakamoto Midori,
Osakama Kazuki,
Nakajima Makoto
Publication year - 2015
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201501084
Subject(s) - chemistry , cyanation , trifluoromethanesulfonate , steric effects , reagent , adduct , oxocarbenium , nuclear magnetic resonance spectroscopy , organic chemistry , medicinal chemistry , combinatorial chemistry , catalysis , nucleophile
The cyanation of acetals and orthoesters by using a sterically congested α‐cyanoamine as a cyanating reagent was investigated. The α‐cyanoamine effectively facilitated cyanation in the presence of trichlorosilyl triflate to produce a variety of cyanated adducts in excellent yields. Analysis of the reaction mixture by 1 H NMR spectroscopy revealed that trichlorosilyl triflate produced an oxocarbenium cation species as an intermediate.