Carbon-Heteroatom Bond-Forming Reactions Mediated by Cerium(IV) Ammonium Nitrate:An Overview

Vijay  Nair; Sreeletha B.  Panicker; Latha G.  Nair; Tesmol G.  George; Anu  Augustine

doi:10.1055/s-2003-36775

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Synlett 2003(2): 0156-0165
DOI: 10.1055/s-2003-36775

ACCOUNT

Carbon-Heteroatom Bond-Forming Reactions Mediated by Cerium(IV) Ammonium Nitrate:An Overview

Vijay Nair*, Sreeletha B. Panicker, Latha G. Nair, Tesmol G. George, Anu Augustine
Organic Chemistry Division, Regional Research Laboratory (CSIR), Trivandrum-695 019, India
Fax: +91(471)491712; e-Mail: gvn@csrrltrd.ren.nic.in;

Further Information

Publication History

Received 10 July 2002
Publication Date:
22 January 2003 (online)

Abstract
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Abstract

As a powerful one-electron oxidant, cerium(IV) ammonium nitrate (CAN) is useful for a variety of oxidative transformations including carbon-carbon bond formation. Recent work has also demonstrated the usefulness of CAN in carbon-heteroatom bond-forming reactions. Particularly noteworthy is the effectiveness of CAN in building C-N, C-S, C-Se, C-Br, and C-I bonds. This account is aimed at creating awareness among organic chemists about such reactions with potential application in the synthesis of a variety of building blocks.

1 Introduction

2 Carbon-Carbon Bond-Forming Reactions Mediated by CAN: A Brief Outline

3 Carbon-Heteroatom Bond-Forming Reactions Mediated by CAN

3.1 Carbon-Nitrogen Bond Formation

3.2 Carbon-Sulfur Bond Formation

3.3 Carbon-Selenium Bond Formation

3.4 Carbon-Halogen Bond Formation

4 Conclusion

Key words

cerium(IV) ammonium nitrate - radical reactions - bond-forming reactions - heteroatoms - oxidations

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