Experimental and computational studies on H2O-promoted, Rh-catalyzed transient-ligand-free ortho-C(sp2)-H amidation of benzaldehydes with dioxazolones
An efficient and convenient ligand-free, rhodium-catalyzed ortho-C(sp2)-H amidation of benzaldehydes with dioxazolones using H2O as the key promoter is described. Using this protocol, a wide range of benzaldehyde substrates were selectively amidated in good to excellent yields with broad functional group compatibility. KIE experiments revealed that the C-H bond activation was likely the rate-limiting step. In addition, computational studies indicated that the catalyst precursor interacted with water and dioxazolones to generate the active catalytic species. Notably, the practicality and efficacy of this method were illustrated by a late-stage amidation of an estrone-derived molecule and further transformations of the amidated product.
Rh-catalyzed Transient Directing Group Promoted C—H Amidation of Benzaldehydes Utilizing Dioxazolones
Transition-metal catalyzed C—H functionalization of benzaldehydes is of great interest in organic synthesis. Herein, we developed a transient directing group assisted amidation of benzaldehydes catalyzed by rhodium catalyst. With the employment of 10 mol% of 4-trifluoromethyl aniline, the in situ generated imine groups as the directing group efficiently enable this transformation. By using this protocol, a wide range of benzaldehydes were efficiently converted into the corresponding N-(2-formylphenyl)benzamides utilizing dioxazolones as the nitrogen source.
Wang, Xiaoyang,Song, Song,Jiao, Ning
supporting information
p. 213 - 216
(2018/01/27)
The first synthesis of 2-amino-1,4-dihydroquinolines
A versatile strategy is described for the synthesis of new 2-amino-1,4-dihydroquinolines. It involved a Knoevenagel condensation of N-protected-2-amino-5-bromobenzaldehyde with ethylcyanoacetate, followed by a cyclization and protection of the NH group to
Viault, Guillaume,Grée, Danielle,Roisnel, Thierry,Chandrasekhar, Srivari,Grée, René
experimental part
p. 10149 - 10154
(2010/02/27)
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