Regioselective decarboxylative direct C-H arylation of boron dipyrromethenes (BODIPYs) at 2,6-positions: a facile access to a diversity-oriented BODIPY library

Liang Luo; Di Wu; Wei Li; Shuai Zhang; Yuanhong Ma; Su Yan; Jingsong You

doi:10.1021/ol502883x

Regioselective decarboxylative direct C-H arylation of boron dipyrromethenes (BODIPYs) at 2,6-positions: a facile access to a diversity-oriented BODIPY library

Org Lett. 2014 Dec 5;16(23):6080-3. doi: 10.1021/ol502883x. Epub 2014 Nov 17.

Authors

Liang Luo¹, Di Wu¹, Wei Li¹, Shuai Zhang¹, Yuanhong Ma¹, Su Yan¹, Jingsong You¹

Affiliation

¹ Key Laboratory of Green Chemistry and Technology of Ministry of Education, College of Chemistry, and State Key Laboratory of Biotherapy, West China Hospital, West China Medical School, Sichuan University, 29 Wangjiang Road, Chengdu 610064, P. R. China.

PMID: 25401990
DOI: 10.1021/ol502883x

Abstract

A palladium-catalyzed regioselective decarboxylative direct C-H arylation of boron dipyrromethenes (BODIPYs) at the 2,6-positions has been developed as a late-stage approach to rapidly assemble a diversity-oriented BODIPY library. With the complement of this protocol, the direct C-H arylation of BODIPYs becomes regiocontrollable at α- and β-positions. A new type of indole-fused BODIPY exhibiting bright red/NIR fluorescence with a large molar extinction coefficient (145,500 M(-1) cm(-1)) and a high quantum yield (71%) has been synthesized for the first time.

Publication types

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

MeSH terms

Boron Compounds / chemical synthesis*
Boron Compounds / chemistry
Catalysis
Combinatorial Chemistry Techniques
Crystallography, X-Ray
Fluorescence
Fluorescent Dyes / chemical synthesis*
Fluorescent Dyes / chemistry
Molecular Structure
Palladium / chemistry
Pyrroles / chemistry*
Stereoisomerism

Substances

4,4-difluoro-4-bora-3a,4a-diaza-s-indacene
Boron Compounds
Fluorescent Dyes
Pyrroles
Palladium