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Flow Technology for Telescoped Generation, Lithiation and Electrophilic (C3) Functionalization of Highly Strained 1‐Azabicyclo[1.1.0]butanes.

Authors :
Musci, Pantaleo
Keutz, Timo
Belaj, Ferdinand
Degennaro, Leonardo
Cantillo, David
Kappe, C. Oliver
Luisi, Renzo
Source :
Angewandte Chemie International Edition; Mar2021, Vol. 60 Issue 12, p6395-6399, 5p
Publication Year :
2021

Abstract

Strained compounds are privileged moieties in modern synthesis. In this context, 1‐azabicyclo[1.1.0]butanes are appealing structural motifs that can be employed as click reagents or precursors to azetidines. We herein report the first telescoped continuous flow protocol for the generation, lithiation, and electrophilic trapping of 1‐azabicyclo[1.1.0]butanes. The flow method allows for exquisite control of the reaction parameters, and the process operates at higher temperatures and safer conditions with respect to batch mode. The efficiency of this intramolecular cyclization/C3‐lithiation/electrophilic quenching flow sequence is documented with more than 20 examples. [ABSTRACT FROM AUTHOR]

Details

Language :
English
ISSN :
14337851
Volume :
60
Issue :
12
Database :
Complementary Index
Journal :
Angewandte Chemie International Edition
Publication Type :
Academic Journal
Accession number :
149130806
Full Text :
https://doi.org/10.1002/anie.202014881