Pd(II)-catalyzed ortho-Hydroxylation and Intramolecular Oxidative C-C Coupling of N-Benzylbenzenesulfonamides

Title
Pd(II)-catalyzed ortho-Hydroxylation and Intramolecular Oxidative C-C Coupling of N-Benzylbenzenesulfonamides
Authors
윤소원
Keywords
Palladium; C–H activation; Hydroxylation; C–C coupling; Sultams
Issue Date
2015-02
Publisher
KOREAN CHEMICAL SOC
Citation
BULLETIN OF THE KOREAN CHEMICAL SOCIETY, v. 36, NO 2, Page. 453-454
Abstract
In recent years, direct activation/functionalization of C—H bonds in aromatic compounds has emerged as an efficient, atom-economical, and eco-friendly synthetic tool, with widespread applications, providing a powerful alternative to the classical coupling reaction using preformed organometallic reagents.[1] Despite the significant development in the past decades, transition-metal-catalyzed functionalization of C(sp2)—H bonds of NH-containing benzylamines has been reported with limited success.[2] Recently, we reported highly effective Pd-catalyzed C—C and/or C—N bond formations via C—H activation of aniline derivatives.[3] Considering the lack of regioselective C(sp2)—H hydroxylation of benzylamines, our continued interest in Pd-catalyzed C—H bond functionalization prompted us to investigate the possibility of a Pd-catalyzed ortho-hydroxylation of NH-containing benzylamines. Here we disclose the discovery of the Pd-catalyzed ortho-hydroxylation[4] and/or intramolecular oxidative C—C coupling of N-benzylsulfonamides depending on the reaction conditions (acid additive and solvent) (Scheme 1).
URI
http://onlinelibrary.wiley.com/doi/10.1002/bkcs.10126/fullhttp://hdl.handle.net/20.500.11754/22457
ISSN
1229-5949; 0253-2964
DOI
http://dx.doi.org/10.1002/bkcs.10126
Appears in Collections:
COLLEGE OF NATURAL SCIENCES[S](자연과학대학) > CHEMISTRY(화학과) > Articles
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