Radical Cyclization of Trichloroacetamides: Synthesis of Lactams

被引：20

作者：

Coussanes, Guilhem ^{[1
]}

Vila, Xavier ^{[1
]}

Diaba, Faiza ^{[1
]}

Bonjoch, Josep ^{[1
]}

机构：

[1] Univ Barcelona, Organ Chem Lab, Fac Pharm, Ave Joan 23 27-31, E-08028 Barcelona, Spain

来源：

SYNTHESIS-STUTTGART | 2017年 / 49卷 / 07期

关键词：

radical reactions; lactams; cyclization; nitrogen heterocycles; hydrides; atom transfer; reduction; haloacetamides; SINGLE-ELECTRON TRANSFER; RUTHENIUM-CATALYZED CYCLIZATION; BOND-FORMING REACTIONS; 1ST TOTAL-SYNTHESIS; POWDER ACETIC-ACID; GAMMA-LACTAMS; N-ALLYLTRICHLOROACETAMIDES; ATRC REACTIONS; STEREOSELECTIVE PREPARATION; REDUCING AGENTS;

D O I：

10.1055/s-0036-1588383

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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)(3)SiH, 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)(3)SiH (TTMSS)-Mediated Reactions 5.3 Borohydride-Mediated Radical Cyclizations 6 Concluding Remarks

引用

页码：1481 / 1499

页数：19

共 137 条

[1] Kinetic Studies of the Initiation Step in Copper Catalyzed Atom Transfer Radical Addition (ATRA) in the Presence of Free Radical Diazo Initiators as Reducing Agents [J].