17079-24-2Relevant articles and documents
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Michalsky et al.
, p. 814,820 (1959)
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Photoinduced, Copper-Catalyzed Decarboxylative C-N Coupling to Generate Protected Amines: An Alternative to the Curtius Rearrangement
Zhao, Wei,Wurz, Ryan P.,Peters, Jonas C.,Fu, Gregory C.
supporting information, p. 12153 - 12156 (2017/09/12)
The Curtius rearrangement is a classic, powerful method for converting carboxylic acids into protected amines, but its widespread use is impeded by safety issues (the need to handle azides). We have developed an alternative to the Curtius rearrangement that employs a copper catalyst in combination with blue-LED irradiation to achieve the decarboxylative coupling of aliphatic carboxylic acid derivatives (specifically, readily available N-hydroxyphthalimide esters) to afford protected amines under mild conditions. This C-N bond-forming process is compatible with a wide array of functional groups, including an alcohol, aldehyde, epoxide, indole, nitroalkane, and sulfide. Control reactions and mechanistic studies are consistent with the hypothesis that copper species are engaged in both the photochemistry and the key bond-forming step, which occurs through out-of-cage coupling of an alkyl radical.
Radical cyanocarbonylation using alkyl allyl sulfone precursors
Kim, Sangmo,Cho, Chang Ho,Kim, Sunggak,Uenoyama, Yoshitaka,Ryu, Ilhyong
, p. 3160 - 3162 (2007/10/03)
Acyl cyanides have been prepared by the three-component coupling reactions comprised of alkyl allyl sulfones, carbon monoxide, and p-tolylsulfonyl cyanide under tin-free radical reaction conditions. Georg Thieme Verlag Stuttgart.
