319921-60-3Relevant articles and documents
Copper-mediated sequential cyanation of aryl C-B and arene C-H bonds using ammonium iodide and DMF
Kim, Jinho,Choi, Jiho,Shin, Kwangmin,Chang, Sukbok
supporting information; experimental part, p. 2528 - 2531 (2012/04/04)
The cyanation of aromatic boronic acids, boronate esters, and borate salts was developed under copper-mediated oxidative conditions using ammonium iodide and DMF as the source of nitrogen and carbon atom of the cyano unit, respectively. The procedure was successfully extended to the cyanation of electron-rich benzenes, and regioselective introduction of a cyano group at the arene C-H bonds was also achieved. The observation that the reaction proceeds via a two-step process, initial iodination and then cyanation, led us to propose that ammonium iodide plays a dual role to provide iodide and nitrogen atom of the cyano moiety.
Straightforward conversion of arene carboxylic acids into aryl nitriles by palladium-catalyzed decarboxylative cyanation reaction
Ouchaou, Kahina,Georgin, Dominique,Taran, Frédéric
experimental part, p. 2083 - 2086 (2010/10/03)
A one-pot procedure to convert aromatic carboxylic acids into aromatic nitriles is described. The methodology is based on a palladium(II)-catalyzed decarboxylative cyanation reaction using cyanohydrins as soluble cyanide sources. The described reaction worked on a panel of substrates and is additionally of particular interest for the straightforward preparation of 13C- or 14C-labeled compounds.
L-proline-promoted Rosenmund-von Braun reaction
Wang, Deping,Kuang, Liping,Li, Zhengwei,Ding, Ke
, p. 69 - 72 (2008/09/21)
L-Proline was identified as an effective additive to promote the Rosenmund-von Braun reaction at a lower temperature (80-120°C). This modified Rosenmund-von Braun cyanation of aryl bromides exhibits excellent functional-group compatibility, and provide an efficient and convenient approach for the synthesis of aryl nitriles. Georg Thieme Verlag Stuttgart.
Sulfinimine-mediated asymmetric synthesis of 1,3-disubstituted tetrahydroisoquinolines: a stereoselective synthesis of cis- and trans-6,8-dimethoxy-1,3-dimethyl-1,2,3,4-tetrahydroisoquinoline.
Davis,Mohanty,Burns,Andemichael
, p. 3901 - 3903 (2007/10/03)
[reaction: see text] The highly diastereoselective addition of lateral lithiated o-tolunitriles to sulfinimines followed by treatment of the resulting sulfinamide with MeLi, hydrolysis, and reduction represents a concise new methodology for the asymmetric
