Oxidative cyanation of N-aryltetrahydroisoquinoline induced by visible light for the synthesis of α-aminonitrile using potassium thiocyanate as a “CN” agent

Abstract

A novel method for the synthesis of α-aminonitrile, through visible-light-induced oxidative cyanation of N-aryltetrahydroisoquinoline with potassium thiocyanate, has been developed.

Electrochemical synthesis of CN-substituted imidazo[1,5-a]pyridines via a cascade process using NH4SCN as both an electrolyte and a non-trivial cyanating agent

“…21,[68][69][70][71] The reaction of pyridine-2-carboxaldehyde 1a with benzylamine 2a leads to imine A, which is then subjected to the addition of a CN anion to the CvN bond, resulting in cyanide B formation. 27,28,32,53,72 The latter transforms into intermediate C via DMSO-mediated oxidation [73][74][75][76][77] or via Shono-type anodic oxidation. [78][79][80] In the next step, intermediate C is isomerized into intermediate D, which undergoes cyclization, providing annulated intermediate E. Finally, anodic or DMSO-mediated oxidation of E leads to the final 1-cyano-imidazo[1,5-a]pyridine 3a.…”

Electron Donor‐Acceptor Complex Enabled Photocyanation of Tertiary Amines with a Stable and User‐Friendly Cyanobenziodoxolone Reagent

“…and α ‐amino alkyl radical was most unlikely involved based on the results of control experiments (see SI for detailed discussion). Our EDA‐complex initiated photocyanation was distinguished for the proposed radical propagation mechanism rather than previous reports on oxidative Strecker‐type mechanism via iminium ion intermediate [9b–h,12,14b] based on a series of rational experiment validations.…”

Electrochemical 2,2,6,6-tetramethylpiperidinyl-N-oxyl (TEMPO)-Mediated α-Cyanation and Phosphonylation of Cyclic Amines with Metal-Free Conditions

“…135.6～137.2 ℃ (Lit. [24] 133～134 ℃). 6,129.7,129.4,128.7,127.1,126.8,126.4,117.9,117.6,53.7,44.3,34.2,31.4,phenyl)-1,2,3,4-tetrahydroisoquinoline-1-carbonitrile (3l): [7e] Yellow oil, 55.2 mg, 95% yield.…”

“…9, 134.6, 129.7, 129.4, 128.7, 127.1, 126.8, 126.4, 117.9, 117.6, 53.7, 44.3, 34.2, 31.4, 28.6. 2-([1,1'-Biphenyl]-4-yl)-1,2,3,4-tetrahydroisoquinoline-1-carbonitrile (3m): [24] Colourless oil, 60.8 mg, 98% yield. 1 6,140.5,134.6,134.5,129.5,129.4,128.9,128.8,128.2,127.1,126.9,126.9,126.7,117.8,117.6,52.9,44.2,-1,2,3,4-tetrahydroisoquinoline-1carbonitrile (3n): [6g] Colourless oil, 38.6 mg, 73% yield.…”