B(C6F5)3-catalyzed divergent cyanosilylations of chromones dependent on temperature

Qiaotian Wang; Xiangqing Feng; Wei Meng; Haifeng Du

doi:10.1039/c9ob01710k

B(C₆F₅)₃-catalyzed divergent cyanosilylations of chromones dependent on temperature

Org Biomol Chem. 2019 Sep 28;17(36):8354-8357. doi: 10.1039/c9ob01710k. Epub 2019 Sep 2.

Authors

Qiaotian Wang¹, Xiangqing Feng¹, Wei Meng¹, Haifeng Du¹

Affiliation

¹ Beijing National Laboratory of Molecular Sciences, CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, China. mengwei@iccas.ac.cn haifengdu@iccas.ac.cn and University of Chinese Academy of Sciences, Beijing 100049, P. R. China.

PMID: 31475277
DOI: 10.1039/c9ob01710k

Abstract

A B(C₆F₅)₃-catalyzed divergent cyanosilylation of chromones has been successfully realized. A variety of 4-oxochromane-2-carbonitriles were furnished as kinetic products in high yields via 1,4-cyanosilylations. An unexpected C-O bond cyanosilylation was achieved when the temperature was raised to 80 °C, affording 4-oxo-4-(2-hydroxylphenyl)but-2-enenitriles as thermodynamic products in 72-94% yields, which was confirmed by DFT results.

Publication types

Research Support, Non-U.S. Gov't