From Isocyanides to Iminonitriles via Silver-mediated Sequential Insertion of C(sp³)-H Bond.

ABSTRACT: Heterocycles are prevalent constituents of many marketing drugs and biologically active molecules to meet modern medical challenges. Isocyanide insertion into C(sp³)-H bonds is challenging especially for the construction of quaternary carbon centers. Herein, we describe an efficient strategy for the synthesis of α-iminonitrile substituted isochromans and tetrahydroisoquinolines (THIQs) with quaternary carbon centers through silver-triflate-mediated sequential isocyanide insertion of C(sp³)-H bonds, where isocyanide acts as the crucial "CN" and "imine" sources. The produced α-iminonitriles have extensive applications as valuable synthetic building blocks for pharmacologically interesting heterocycles. This protocol could be further applied for the synthesis of iminonitrile-decorated phenanthridines and azapyrene. Interestingly, a remarkable aggregation-induced emission (AIE) effect was first observed for an iminonitrile-decorated pyrene derivative, which may open a particular area for iminonitrile applications in materials science.

SUBMITTER: Chi H 

PROVIDER: S-EPMC6859232 | biostudies-literature | 2019 Nov

REPOSITORIES: biostudies-literature