Pd(II)-Catalyzed o-C-H Acetoxylation of Phenylalanine and Ephedrine Derivatives with MeCOOOtBu/Ac2O

被引:131
作者
Vickers, Chris J. [1 ]
Mei, Tian-Sheng [1 ]
Yu, Jin-Quan [1 ]
机构
[1] Scripps Res Inst, Dept Chem, La Jolla, CA 92037 USA
基金
美国国家科学基金会;
关键词
PALLADIUM(II)-MEDIATED OXIDATION; COUPLING REACTIONS; FUNCTIONALIZATION; CATALYST; BONDS; ACTIVATION; OXIDANT; PD(II); ARENES; MILD;
D O I
10.1021/ol1007108
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Pd(II)-catalyzed ortho C-H acetoxylation of triflate protected phenethyl- and phenpropylamines has been achieved with tert-butyl peroxyacetate as the stoichiometric oxidant and either DMF or CH3CN as the promoter. The reaction was found to tolerate a large variety of functional groups and could be combined with subsequent intramolecular amination to afford functionalized indoline derivatives.
引用
收藏
页码:2511 / 2513
页数:3
相关论文
共 36 条
[21]  
2-E
[22]   Novel acetoxylation and C-C coupling reactions at unactivated positions in α-amino acid derivatives [J].
Reddy, B. V. Subba ;
Reddy, Leleti Rajender ;
Corey, E. J. .
ORGANIC LETTERS, 2006, 8 (15) :3391-3394
[23]   In vitro characterization of ephedrine-related stereoisomers at biogenic amine transporters and the receptorome reveals selective actions as norepinephrine transporter substrates [J].
Rothman, RB ;
Vu, N ;
Partilla, JS ;
Roth, BL ;
Hufeisen, SJ ;
Compton-Toth, BA ;
Birkes, J ;
Young, R ;
Glennon, RA .
JOURNAL OF PHARMACOLOGY AND EXPERIMENTAL THERAPEUTICS, 2003, 307 (01) :138-145
[24]   Direct transition metal-catalyzed functionalization of heteroaromatic compounds [J].
Seregin, Ilya V. ;
Gevorgyan, Vladimir .
CHEMICAL SOCIETY REVIEWS, 2007, 36 (07) :1173-1193
[25]   Direct effects of ephedrine isomers on human β-adrenergic receptor subtypes [J].
Vansal, SS ;
Feller, DR .
BIOCHEMICAL PHARMACOLOGY, 1999, 58 (05) :807-810
[26]   Ligand-enabled PtII-C(sp3) bond functionalization with dioxygen as a direct oxidant [J].
Vedernikov, Andrei N. .
CHEMICAL COMMUNICATIONS, 2009, (32) :4781-4790
[27]   Palladium-catalyzed oxidation of Boc-protected N-methylamines with IOAc as the oxidant:: A Boc-directed sp3 C-H bond activation [J].
Wang, Dong-Hui ;
Hao, Xue-Shi ;
Wu, Di-Fu ;
Yu, Jin-Quan .
ORGANIC LETTERS, 2006, 8 (15) :3387-3390
[28]   Direct ortho-acetoxylation of anilides via palladium-catalyzed sp2 C-H bond oxidative activation [J].
Wang, Guan-Wu ;
Yuan, Ting-Ting ;
Wu, Xue-Liang .
JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (12) :4717-4720
[29]   Versatile Pd(OTf)2.2H2O-Catalyzed ortho-Fluorination Using NMP as a Promoter [J].
Wang, Xisheng ;
Mei, Tian-Sheng ;
Yu, Jin-Quan .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (22) :7520-+
[30]   Regioselective intramolecular oxidation of unactivated C-H bonds by dioxiranes generated in situ [J].
Yang, D ;
Wong, MK ;
Wang, XC ;
Tang, YC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (26) :6611-6612