BODIPY‐Labeled Cyclobutanes by Secondary C(sp3)−H Arylations for Live‐Cell Imaging

Arylated cyclobutanes were accessed by a versatile palladium‐catalyzed secondary C(sp3)−H activation, exploiting chelation assistance by modular triazoles. The C−H arylation led to cyclobutane natural product derivatives in a highly regioselective fashion, setting the stage for the easy access to no...

Full description

Saved in:
Bibliographic Details
Published in:Chemistry : a European journal 2019-10, Vol.25 (55), p.12712-12718
Main Authors: Virelli, Matteo, Wang, Wei, Kuniyil, Rositha, Wu, Jun, Zanoni, Giuseppe, Fernandez, Antonio, Scott, Jamie, Vendrell, Marc, Ackermann, Lutz
Format: Article
Language:English
Subjects:
BODIPY
Boron
Boron Compounds
C(sp3)−H activation
Catalysis
Cell Tracking - methods
Chelating Agents - chemistry
Chelation
Chemistry
Cyclobutane
cyclobutanes
Cyclobutanes - chemistry
labeling
Molecular Structure
Natural products
Optical Imaging - methods
Palladium
Palladium - chemistry
Triazoles
Triazoles - chemistry
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:Arylated cyclobutanes were accessed by a versatile palladium‐catalyzed secondary C(sp3)−H activation, exploiting chelation assistance by modular triazoles. The C−H arylation led to cyclobutane natural product derivatives in a highly regioselective fashion, setting the stage for the easy access to novel fluorogenic boron‐dipyrrin (BODIPY)‐labeled probes for live‐cell imaging. Suitable for live‐cell imaging: An unprecedented secondary C(sp3)−H arylation by TAM assistance has been reported, which provides access to functionalized cyclobutane natural product analogues. This strategy features an excellent functional‐group tolerance and a broad substrate scope. Moreover, the first cyclobutane‐BODIPY derivatives have been prepared, proving its synthetic utility.
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.201903461