Iron-catalyzed peroxidation-carbamoylation of alkenes with hydroperoxides and formamides via formyl C(sp2)-H functionalization

被引:34
作者
Cheng, Jun-Kee [2 ]
Shen, Liang [2 ]
Wu, Liu-Hai [2 ]
Hu, Xu-Hong [1 ]
Loh, Teck-Peng [1 ,2 ]
机构
[1] Nanjing Tech Univ, Jiangsu Natl Synerget Innovat Ctr Adv Mat, Sch Chem & Mol Engn, Inst Adv Synth, Nanjing 211816, Jiangsu, Peoples R China
[2] Nanyang Technol Univ, Sch Phys & Math Sci, Div Chem & Biol Chem, Singapore 637371, Singapore
基金
新加坡国家研究基金会;
关键词
MONOXIDE-FREE AMINOCARBONYLATION; N-SUBSTITUTED FORMAMIDES; CARBON-CENTERED RADICALS; BOND FORMATION; CARBONYLATION-PEROXIDATION; C-H; 1,4-DICARBONYL COMPOUNDS; ORGANIC-SYNTHESIS; ARYL ISONITRILES; DIRECT ADDITION;
D O I
10.1039/c7cc08074c
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A reaction protocol in which FeCl3 and tert-butyl hydroperoxide facilitated a selective radical coupling reaction of aryl alkenes or 1,3-enynes with tert-butyl hydroperoxide and formamides to prepare an array of beta-peroxy amides has been achieved. The beta-peroxy amide could serve as a synthetic precursor which was facilely converted to beta-hydroxy amide, beta-keto amide and beta-lactam following subsequent chemical transformation.
引用
收藏
页码:12830 / 12833
页数:4
相关论文
共 81 条
[1]   Palladium-catalyzed ring-forming aminoacetoxylation of alkenes [J].
Alexanian, EJ ;
Lee, C ;
Sorensen, EJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (21) :7690-7691
[2]   Radical chemistry of tert-butyl hydroperoxide (TBHP).: Part 1.: Studies of the FeIII-TBHP mechanism [J].
Barton, DHR ;
Le Gloahec, VN ;
Patin, H ;
Launay, F .
NEW JOURNAL OF CHEMISTRY, 1998, 22 (06) :559-563
[3]   Osmium-free direct syn-dihydroxylation of alkenes [J].
Bataille, Carole J. R. ;
Donohoe, Timothy J. .
CHEMICAL SOCIETY REVIEWS, 2011, 40 (01) :114-128
[4]   C-C, C-O, C-N bond formation on sp2 carbon by Pd(II)-catalyzed reactions involving oxidant agents [J].
Beccalli, Egle M. ;
Broggini, Gianluigi ;
Martinelli, Michela ;
Sottocornola, Silvia .
CHEMICAL REVIEWS, 2007, 107 (11) :5318-5365
[5]   N-bromoacetamide - A new nitrogen source for the catalytic asymmetric aminohydroxylation of olefins [J].
Bruncko, M ;
Schlingloff, G ;
Sharpless, KB .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1997, 36 (13-14) :1483-1486
[6]  
Cardona F, 2009, NAT CHEM, V1, P269, DOI [10.1038/nchem.256, 10.1038/NCHEM.256]
[7]   Copper-Catalyzed Intermolecular Carboetherification of Unactivated Alkenes by Alkyl Nitriles and Alcohols [J].
Chatalova-Sazepin, Claire ;
Wang, Qian ;
Sammis, Glenn M. ;
Zhu, Jieping .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (18) :5443-5446
[8]   Copper- and Cobalt-Catalyzed Direct Coupling of sp3 α-Carbon of Alcohols with Alkenes and Hydroperoxides [J].
Cheng, Jun-Kee ;
Loh, Teck-Peng .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (01) :42-45
[9]   Magnesium/methanol: Sn effective reducing agent for peroxides [J].
Dai, P ;
Dussault, PH ;
Trullinger, TK .
JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (08) :2851-2852
[10]   Transition-Metal-Catalyzed Diamination of Olefins [J].
de Figueiredo, Renata Marcia .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (07) :1190-1193