Synlett 2020; 31(18): 1747-1752
DOI: 10.1055/s-0040-1707271
synpacts

Redox-Neutral Propargylic C–H Functionalization by Using Iron Catalysis

Austin C. Durham
,
Yidong Wang
,
We thank the University of Pittsburgh for generous startup support.


Abstract

In spite of their rich stoichiometric chemistry, cyclopentadienyliron(II) dicarbonyl complexes are rarely used as catalysts in organic synthesis. Inspired by precedents in the chemistry of cationic olefin complexes and neutral allylmetal species, our group has developed a coupling of alkynes or alkenes with aldehydes and other carbonyl electrophiles to give homopropargylic and homoallylic alcohols, respectively, by using a substituted cyclopentadienyliron(II) dicarbonyl complex as the catalyst. In this article, we first contextualize this development within the conceptual background of C–H functionalization chemistry and relative to key stoichiometric precedents. We then give an account of our group’s discovery and development of the catalytic α-functionalization of alkenes and alkynes with electrophilic reagents.

Introduction

Preliminary Stoichiometric Work

Hydroxyalkylation Development and Scope

Conclusions and Future Directions

Supporting Information



Publication History

Received: 23 June 2020

Accepted after revision: 20 July 2020

Publication Date:
08 September 2020 (online)

© 2020. Thieme. All rights reserved

Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany

 
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