Synthesis 2017; 49(07): 1481-1499
DOI: 10.1055/s-0036-1588383
short review
© Georg Thieme Verlag Stuttgart · New York

Radical Cyclization of Trichloroacetamides: Synthesis of Lactams

Guilhem Coussanes
,
Xavier Vila
,
Faïza Diaba
,
Josep Bonjoch*
Further Information

Publication History

Received: 07 October 2016

Accepted after revision: 01 December 2016

Publication Date:
03 January 2017 (online)


Abstract

Trichloroacetamides can act as radical precursors to synthesize nitrogen-containing heterocycles in a variety of processes, mainly involving atom transfer radical cyclizations (ATRC), mediated by Cu(I) or Ru(II) catalysts, and the hydride reductive method, employing either Bu3SnH or (Me3Si)3SiH, or recently NaBH3CN. Additionally, amine-mediated single-electron transfer cyclizations, as well as radical processes promoted by Ni, Fe, Mn, Ti, and Ag, have been developed.

1 Introduction

2 Atom Transfer Radical Cyclizations (ATRC)

2.1 Copper-Mediated Reactions

2.2 Ruthenium(II)-Mediated Reactions

2.3 ATRC Promoted by Other Metals

3 Photocyclization Reactions

4 Reductive Cyclization via Single-Electron Transfer Processes

4.1 Ni/AcOH-Promoted Cyclizations

4.2 Titanocene(III)-Catalyzed Reactions

4.3 Silver Acetate Mediated Reactions

4.4 Amine-Mediated Single-Electron Transfer

5 Cyclization Involving M–H Hydrogen Atom Donors (M = Sn, Si, B)

5.1 Bu3SnH-Mediated Reactions

5.2 (Me3Si)3SiH (TTMSS)-Mediated Reactions

5.3 Borohydride-Mediated Radical Cyclizations

6 Concluding Remarks

 
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