Annulative π-extension of BODIPYs made easy via gold(i)-catalyzed cycloisomerization.

ABSTRACT: Here we report gold(i)-catalyzed cycloisomerization as a new powerful synthetic tool for the preparation of π-extended BODIPY derivatives. The catalytic system PPh^F ₃AuCl/AgSbF₆ enables the synthesis of [b]-[2,1]naphtho-fused-BODIPYs (2a-2c) under mild conditions, in excellent yields and short reaction times. The reaction is totally regioselective to the 6-endo-dig product and for the α-position of the BODIPY, which is both the kinetically and thermodynamically favored pathway, as supported by the free energy profile calculated by means of Density Functional Theory (DFT). Moreover, this methodology also allows the synthesis of two new families of [b]-aryl-fused-BODIPYs, namely, [3,4]phenanthro- (2e and 2f) and [1,2]

SUBMITTER: Labella J 

PROVIDER: S-EPMC8162369 | biostudies-literature | 2020 Jun

REPOSITORIES: biostudies-literature