Open AccessModular Synthetic Approach to Silicon-Rhodamine Homologues and Analogues via Bis-aryllanthanum Reagents
Author(s) -
Alexey N. Butkevich
Publication year - 2021
Publication title -
organic letters
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.94
H-Index - 239
eISSN - 1523-7060
pISSN - 1523-7052
DOI - 10.1021/acs.orglett.1c00512
Subject(s) - chemistry , regioselectivity , fluorophore , reagent , rhodamine , tandem , combinatorial chemistry , nucleophile , fluorescence , modular design , functional group , allene , organic chemistry , catalysis , computer science , physics , materials science , polymer , quantum mechanics , composite material , operating system
A modular synthetic approach toward diverse analogues of the far-red fluorophore silicon-rhodamine (SiR), based on a regioselective double nucleophilic addition of aryllanthanum reagents to esters, anhydrides, and lactones, is proposed. The reaction has improved functional group tolerance and represents a unified strategy toward cell-permeant, spontaneously blinking, and photoactivatable SiR fluorescent labels. In tandem with Pd-catalyzed hydroxy- or aminocarbonylation, it serves a streamlined synthetic pathway to a series of validated live-cell-compatible fluorescent dyes.