Palladium-Catalyzed Z-Selective Oxidative Amination of ortho-Substituted Primary Anilines with Olefins under an Open Air Atmosphere

被引：48

作者：

Mizuta, Yohei ^{[1
]}

Yasuda, Kaoru ^{[1
]}

Obora, Yasushi ^{[1
]}

机构：

[1] Kansai Univ, Fac Chem Mat & Bioengn, Dept Chem & Mat Engn, Suita, Osaka 5648680, Japan

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2013年 / 78卷 / 12期

关键词：

C-H AMINATION; CIS-AMINOPALLADATION; EFFICIENT SYNTHESIS; MOLECULAR-OXYGEN; FACILE SYNTHESIS; ALKENES; CYCLIZATION; FUNCTIONALIZATION; ACTIVATION; REACTIVITY;

D O I：

10.1021/jo4010734

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The Pd-catalyzed oxidative amination of olefins with primary anilines has been achieved using molecular dioxygen as the sole oxidant. The use of ortho-substituted primary anilines such as ortho-toluidine was the key to the successful development of this reaction, providing the corresponding N-alkenyl substituted anilines in high yields with unusually high levels of Z-selectivity.

引用

页码：6332 / 6337

页数：6

共 50 条

[1] Fast, easy, solvent-free, microwave-promoted Michael addition of anilines to α,β-unsaturated alkenes:: synthesis of N-aryl functionalized β-amino esters and acids
Amore, Kristen M.
Leadbeater, Nicholas E.
Miller, Tyson A.
Schmink, Jason R.
[J]. TETRAHEDRON LETTERS, 2006, 47 (48) : 8583 - 8586
[2] Beller M, 1999, CHEM-EUR J, V5, P1306, DOI 10.1002/(SICI)1521-3765(19990401)5:4<1306::AID-CHEM1306>3.0.CO
[3] 2-4
[4] Anti-Markovnikov functionalization of olefins: Rhodium-catalyzed oxidative aminations of styrenes
Beller, M
Eichberger, M
Trauthwein, H
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1997, 36 (20): : 2225 - 2227
[5] Synthesis of Bicyclic N-Arylmethyl-Substituted Iminoribitol Derivatives as Selective Nucleoside Hydrolase Inhibitors
Berg, Maya
Bal, Gunther
Goeminne, Annelies
Van der Veken, Pieter
Versees, Wirn
Steyaert, Jan
Haemers, Achiel
Augustyns, Koen
[J]. CHEMMEDCHEM, 2009, 4 (02) : 249 - 260
[6] RhIII-Catalyzed Oxidative Olefination of Vinylic C-H Bonds: Efficient and Selective Access to Di-unsaturated α-Amino Acid Derivatives and Other Linear 1,3-Butadienes
Besset, Tatiana
Kuhl, Nadine
Patureau, Frederic W.
Glorius, Frank
[J]. CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (26) : 7167 - 7171
[7] Selective Pd-catalyzed oxidative coupling of anilides with olefins through C-H bond activation at room temperature
Boele, MDK
van Strijdonck, GPF
de Vries, AHM
Kamer, PCJ
de Vries, JG
van Leeuwen, PWNM
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (08) : 1586 - 1587
[8] PALLADIUM-ASSISTED FUNCTIONALIZATION OF OLEFINS - A NEW AMINATION OF ELECTRON-DEFICIENT OLEFINS
BOZELL, JJ
HEGEDUS, LS
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (12) : 2561 - 2563
[9] Aerobic oxidative amination of unactivated alkenes catalyzed by palladium
Brice, JL
Harang, JE
Timokhin, VI
Anastasi, NR
Stahl, SS
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (09) : 2868 - 2869
[10] syn-1,2-amino alcohols via diastereoselective allylic C-H amination
Fraunhoffer, Kenneth J.
White, M. Christina
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (23) : 7274 - +

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