[FeIII(TF4DMAP)OTf] catalysed anti-Markovnikov oxidation of terminal aryl alkenes to aldehydes and transformation of methyl aryl tertiary amines to formamides with H2O2 as a terminal oxidant

被引:48
作者
Du, Yi-Dan [1 ]
Tse, Chun-Wai [2 ,3 ]
Xu, Zhen-Jiang [1 ]
Liu, Yungen [2 ,3 ]
Che, Chi-Ming [1 ,2 ,3 ]
机构
[1] Shanghai Inst Organ Chem, Shanghai Hong Kong Joint Lab Chem Synth, Shanghai, Peoples R China
[2] Univ Hong Kong, Dept Chem, Hong Kong, Hong Kong, Peoples R China
[3] Univ Hong Kong, State Key Lab Synthet Chem, Hong Kong, Hong Kong, Peoples R China
关键词
WACKER-TYPE OXIDATION; MOLECULAR-OXYGEN; EPOXIDATION-ISOMERIZATION; PORPHYRIN COMPLEXES; AEROBIC OXIDATION; ORGANIC-SYNTHESIS; OLEFINS; REACTIVITY; METALLOPORPHYRIN; REARRANGEMENT;
D O I
10.1039/c4cc05972g
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Anti-Markovnikov oxidation of terminal aryl alkenes to aldehydes and transformation of N-methyl aryl tertiary amines to formamides with H2O2 as a terminal oxidant under mild conditions have been achieved with moderate to good product yields using [Fe-III(TF(4)DMAP)OTf] as catalyst.
引用
收藏
页码:12669 / 12672
页数:4
相关论文
共 45 条
[1]   Iron-catalyzed reactions in organic synthesis [J].
Bolm, C ;
Legros, J ;
Le Paih, J ;
Zani, L .
CHEMICAL REVIEWS, 2004, 104 (12) :6217-6254
[2]   Selective oxidation of terminal aryl and aliphatic alkenes to aldehydes catalyzed by iron(III) porphyrins with triflate as a counter anion [J].
Chen, Guo-Qiang ;
Xu, Zhen-Jiang ;
Zhou, Cong-Ying ;
Che, Chi-Ming .
CHEMICAL COMMUNICATIONS, 2011, 47 (39) :10963-10965
[3]   A practical and mild method for the highly selective conversion of terminal alkenes into aldehydes through epoxidation-isomerization with ruthenium(IV)-porphyrin catalysts [J].
Chen, J ;
Che, CM .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (37) :4950-4954
[4]   A predictably selective aliphatic C-H oxidation reaction for complex molecule synthesis [J].
Chen, Mark S. ;
White, M. Christina .
SCIENCE, 2007, 318 (5851) :783-787
[5]   Combined Effects on Selectivity in Fe-Catalyzed Methylene Oxidation [J].
Chen, Mark S. ;
White, M. Christina .
SCIENCE, 2010, 327 (5965) :566-571
[6]   An iron catalyzed regioselective oxidation of terminal alkenes to aldehydes [J].
Chowdhury, Abhishek Dutta ;
Ray, Ritwika ;
Lahiri, Goutam Kumar .
CHEMICAL COMMUNICATIONS, 2012, 48 (44) :5497-5499
[7]   Iron-catalysed carbon-heteroatom and heteroatom-heteroatom bond forming processes [J].
Correa, Arkaitz ;
Mancheno, Olga Garcia ;
Bolm, Carsten .
CHEMICAL SOCIETY REVIEWS, 2008, 37 (06) :1108-1117
[8]   Studies Toward Communesin F: A Diels-Alder Approach [J].
Danielsson, Jakob ;
Somfai, Peter .
ORGANIC LETTERS, 2014, 16 (03) :784-787
[9]   Primary Alcohols from Terminal Olefins: Formal Anti-Markovnikov Hydration via Triple Relay Catalysis [J].
Dong, Guangbin ;
Teo, Peili ;
Wickens, Zachary K. ;
Grubbs, Robert H. .
SCIENCE, 2011, 333 (6049) :1609-1612
[10]   Iron-Catalyzed Asymmetric Aerobic Oxidation: Oxidative Coupling of 2-Naphthols [J].
Egami, Hiromichi ;
Katsuki, Tsutomu .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (17) :6082-+