Synthesis and structure of hypervalent diacetoxybromobenzene and aziridination of olefins with imino-λ3-bromane generated in situ under metal-free conditions.

作者: Md. Mahbubul Hoque , Kazunori Miyamoto , Norihiro Tada , Motoo Shiro , Masahito Ochiai

DOI: 10.1021/OL201868N

关键词: Medicinal chemistryHypervalent moleculeMoleculeYield (chemistry)Intramolecular forceOrganic chemistryBenzeneCatalysisLigandIn situChemistry

摘要: Ligand exchange of p-CF3C6H4BrF2 with acetoxy groups using AcOH and Ac2O affords (diacetoxybromo)benzene in a high yield, which undergoes aziridination alkenes the presence TfNH2 sulfamate esters one pot under mild conditions. The proceeds stereospecifically retention stereochemistry olefins at room temperature limiting amounts transition-metal-free one-pot procedure can be applied to intramolecular versions.

参考文章(53)
Kiran Guthikonda, J. Du Bois, A Unique and Highly Efficient Method for Catalytic Olefin Aziridination Journal of the American Chemical Society. ,vol. 124, pp. 13672- 13673 ,(2002) , 10.1021/JA028253A
Kiran Guthikonda, Paul M. Wehn, Brian J. Caliando, J. Du Bois, Rh-catalyzed alkene oxidation: a highly efficient and selective process for preparing N-alkoxysulfonyl aziridines Tetrahedron. ,vol. 62, pp. 11331- 11342 ,(2006) , 10.1016/J.TET.2006.07.099
Masahito Ochiai, Akira Yoshimura, Takeshi Mori, Yoshio Nishi, Masaya Hirobe, Difluoro-λ3-Bromane-Induced Oxidative Carbon−Carbon Bond-Forming Reactions: Ethanol as an Electrophilic Partner and Alkynes as Nucleophiles Journal of the American Chemical Society. ,vol. 130, pp. 3742- 3743 ,(2008) , 10.1021/JA801097C
John J. Reilly, David J. Duncan, Timothy P. Wunz, Robert A. Patsiga, Isolation and properties of acetyl hypobromite Journal of Organic Chemistry. ,vol. 39, pp. 3291- 3292 ,(1974) , 10.1021/JO00936A032
David N. Zalatan, J. Du Bois, Understanding the differential performance of Rh2(esp)2 as a catalyst for C-H amination. Journal of the American Chemical Society. ,vol. 131, pp. 7558- 7559 ,(2009) , 10.1021/JA902893U
Masahito Ochiai, Takao Kaneaki, Norihiro Tada, Kazunori Miyamoto, Hiroshi Chuman, Motoo Shiro, Satoko Hayashi, Waro Nakanishi, A new type of imido group donor : Synthesis and characterization of sulfonylimino-λ3-bromane that acts as a nitrenoid in the aziridination of olefins at room temperature under metal-free conditions Journal of the American Chemical Society. ,vol. 129, pp. 12938- 12939 ,(2007) , 10.1021/JA075811I
Masahito Ochiai, Kazunori Miyamoto, Satoko Hayashi, Waro Nakanishi, Hypervalent N-sulfonylimino-λ3-bromane: active nitrenoid species at ambient temperature under metal-free conditions Chemical Communications. ,vol. 46, pp. 511- 521 ,(2010) , 10.1039/B922033J
Hermann Josef Frohn, Matthias Giesen, Beitrage zur chemie des bromtrifluorids 1. Teil pentafluorphenylbrom(III)difluorid und -bis (trifluoracetat) Journal of Fluorine Chemistry. ,vol. 24, pp. 9- 15 ,(1984) , 10.1016/S0022-1139(00)81292-0