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Updated: Nov 5, 2025

Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy
Published on: November 9, 2019
Facile Synthesis of Cyanide and Isocyanides from CO
Maotong Xu1, Bastiaan Kooij1,2, Tongtong Wang1,3
1Department of Chemistry, University of Toronto, 80 St. George St., Toronto, Ontario, M5S3H6, Canada.
Abstract:
The reaction of K[N(SiMe3 )2 ] with 13 CO proceeds in C6 D6 or THF affording K13 CN and O(SiMe3 )2 under mild conditions as confirmed by crystallographic characterization of K(18-crown-6)CN. Similarly reaction of the alkali metal amides, M[N(SiR3 )R'] (M=Li, K; R=Ph, Me; R'=alkyl, aryl) provides the corresponding 13 C labeled isocyanide RN13 C and MOSiR3 , generally in high yields. In some instances, the use of the sterically bulky Ph3 Si-substituent is required to preclude 1,2-silyl migration affording the silylcarbamoyl salt M[Me3 SiC(O)NR']. These reactions have been used to obtain 19 examples of 13 C labelled isocyanides, and several examples of gram scale reactions are reported. The mechanism of the reactions is probed via reliable DFT calculations.
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