Synlett
DOI: 10.1055/s-0036-1590900
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© Georg Thieme Verlag Stuttgart · New York

Recent Synthetic Applications of Catalyst-Free Photochemistry

Wenbo Liu, Chao-Jun Li*
  • Department of Chemistry and FQRNT Centre for Green Chemistry and Catalysis, McGill University, 801 Sherbrooke St. W., Montreal, Quebec H3A 0B8, Canada   Email: cj.li@mcgill.ca
We are grateful to the Canada Research Chair Foundation (to C.-J. Li), the CFI, FQRNT Center for Green Chemistry and Catalysis, NSERC, and McGill University for support of our research. W. Liu thanks McGill Chemistry for a Major Scholarship and CIHR for a Drug Development Training Program Scholarship.
Further Information

Publication History

Received: 18 June 2017

Accepted after revision: 07 August 2017

Publication Date:
14 September 2017 (eFirst)

Dedicated to Professor Victor Snieckus on the occasion of his 80th birthday

Abstract

Catalyst-free photochemistry provides numerous opportunities toward sustainable synthesis because catalyst separation can usually be avoided, which is consistent with green chemistry principles. Complementary to the well-reviewed photoredox chemistry, this review specifically summarizes the synthetic applications of photochemistry without external catalysts reported since 2000. The selected examples include both natural product synthesis and new methodology development. This review is arranged based on the type of chromophore. It is our hope that this review will inspire more synthetic chemists to embrace photochemistry into their research plans.

1 Introduction

2 Photochemistry of Olefins

2.1 [2+2] Cycloaddition of Enones and Olefins

2.2 Cycloaddition of Olefins without Carbonyl Groups

2.3 Z/E Isomerization

2.4 Cyclization

2.5 Others

3 Photochemistry of C=O

3.1 The Paternò–Büchi Reaction

3.2 The Yang Photoenolization

3.3 The Norrish Type I Reaction

3.4 The Norrish Type II Reaction

3.5 Others

4 Photochemistry of Nitrogen-Containing Functional Groups

5 Photochemistry of Halogen-Containing Compounds

6 Conclusion and Outlook