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Flow chemistry as a discovery tool to access sp2-sp3 cross-coupling reactions via diazo compounds.


Type

Article

Change log

Authors

Tran, Duc N 
Battilocchio, Claudio  ORCID logo  https://orcid.org/0000-0002-4601-8527
Lou, Shing-Bong 
Hawkins, Joel M 
Ley, Steven V 

Abstract

The work takes advantage of an important feature of flow chemistry, whereby the generation of a transient species (or reactive intermediate) can be followed by a transfer step into another chemical environment, before the intermediate is reacted with a coupling partner. This concept is successfully applied to achieve a room temperature sp2-sp3 cross coupling of boronic acids with diazo compounds, these latter species being generated from hydrazones under flow conditions using MnO2 as the oxidant.

Description

Keywords

0306 Physical Chemistry (incl. Structural)

Journal Title

Chem Sci

Conference Name

Journal ISSN

2041-6520
2041-6539

Volume Title

6

Publisher

Royal Society of Chemistry (RSC)
Sponsorship
Engineering and Physical Sciences Research Council (EP/K009494/1)
Engineering and Physical Sciences Research Council (EP/K039520/1)
We are grateful to the Swiss National Science Foundation (DNT), Pfizer Worldwide Research and Development (CB and JMH), and the EPSRC (SVL, grant nº EP/K0099494/1) for financial support.