Substrate-Assisted Carbon Dioxide Activation as a Versatile Approach for Heterocyclic Synthesis

Jeroen Rintjema; Arjan W. Kleij

doi:10.1055/s-0035-1562520

Synthesis, Table of Contents

Synthesis 2016; 48(22): 3863-3878
DOI: 10.1055/s-0035-1562520

short review

Substrate-Assisted Carbon Dioxide Activation as a Versatile Approach for Heterocyclic Synthesis

Jeroen Rintjema

^aInstitute of Chemical Research of Catalonia (ICIQ), the Barcelona Institute of Science and Technology, Av. Països Catalans 16, 43007 Tarragona, Spain Email: akleij@iciq.es

,

Arjan W. Kleij*

^aInstitute of Chemical Research of Catalonia (ICIQ), the Barcelona Institute of Science and Technology, Av. Països Catalans 16, 43007 Tarragona, Spain Email: akleij@iciq.es

^bCatalan Institute of Research and Advanced Studies (ICREA), Pg. Lluis Companys 23, 08010 Barcelona, Spain

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Abstract

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Abstract

The incorporation of CO₂ into substrates containing alcohol or amine functional groups displays interesting substrate-controlled reactivity, both in terms of providing milder reaction conditions and the potential towards new reactivity modes. Various heterocyclic structures can be prepared using this substrate-driven approach starting from functional derivatives of (homo)allylic and propargylic alcohols/amines, epoxy alcohols, and hydroxy-oxetanes among others. This review summarizes the recent advances made in this area.

1 Introduction

2 Catalytic Conversion of Propargylic Alcohols

3 Catalytic Conversion of Propargylic Amines

4 Homoallylic and Allylic Alcohol Substrate Conversions

5 Transformation of Allylic Amines

6 Epoxy Alcohols/Amines as Substrates

7 Hydroxy-Substituted Oxetane and Azetidine Scaffolds

8 Conversion of Other Substrates

9 Summary and Outlook

Key words

amine - alcohols - carbon dioxide - heterocycles - homogeneous catalysis - substrate activation

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References

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