B(C6F5)3-catalyzed divergent cyanosilylations of chromones dependent on temperature. Issue 36 (2nd September 2019)

• Record Type: Journal Article
• Authors: Wang, Qiaotian; Feng, Xiangqing; Meng, Wei; Du, Haifeng
• Is Part Of: Organic & biomolecular chemistry. Volume 17:Issue 36(2019)
• Page Start: 8354
• Page End: 8357
• Publication Date: 2019-09-02
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/c9ob01710k
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : A B(C6 F5 )3 -catalyzed divergent cyanosilylation of chromones dependent on temperature has been realized to afford the corresponding products in good to high yields. Abstract : A B(C6 F5 )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.