Radical Cyclization of Trichloroacetamides: Synthesis of Lactams

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

Key words

radical reactions - lactams - cyclization - nitrogen heterocycles - hydrides - atom transfer - reduction - haloacetamides

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