Preparation of Functionalized Amides Using Dicarbamoylzincs.

Authors :: Djukanovic D
Ganiek MA
Nishi K
Karaghiosoff K
Mashima K
Knochel P
Source :: Angewandte Chemie (International ed. in English) [Angew Chem Int Ed Engl] 2022 Aug 01; Vol. 61 (31), pp. e202205440. Date of Electronic Publication: 2022 Jun 13.
Publication Year :: 2022
Abstract: We report a new convenient preparation of dicarbamoylzincs of type (R <superscript>1</superscript> R <superscript>2</superscript> NCO) <subscript>2</subscript> Zn by the treatment of ZnCl <subscript>2</subscript> and formamides R <superscript>1</superscript> R <superscript>2</superscript> NCHO with LiTMP in THF (15 °C, 15 min) or by the reaction of formamides R <superscript>1</superscript> R <superscript>2</superscript> NCHO with TMP <subscript>2</subscript> Zn (25 °C, 16 h). This second method tolerates sensitive groups such as an ester, ketone or nitro function. Reaction of these dicarbamoylzincs with allylic, benzylic, aryl, alkenyl bromides, acid chlorides, aldehydes or enones provided various polyfunctional amides in 47-97 % yields. <superscript>13</superscript> C NMR characterization of these new carbamoylzinc derivatives is reported.<br /> (© 2022 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH.)