Cu(OAc)2-Catalysed Oxidative Dual C-H/N-H Activation of Terminal Alkynes and N-Deprotected Sulfonimidamides: An Easy Access to N-Alkynylated Sulfonimidamides

• Published in: European journal of organic chemistry Vol. 2015; no. 13; pp. 2861 - 2867
• Main Authors: Nandi, Ganesh Chandra, Kota, Sudhakar Rao, Naicker, Tricia, Govender, Thavendran, Kruger, Hendrick G., Arvidsson, Per I.
• Format: Journal Article
• Language: English
• Published: Weinheim WILEY-VCH Verlag 01.05.2015; WILEY‐VCH Verlag; Wiley; Wiley Subscription Services, Inc
• Subjects: Alkynes; C-H activation; C-N coupling; Chemistry; Chemistry, Organic; Copper; Medicin och hälsovetenskap; Physical Sciences; Science & Technology; Sulfonimidamides; Sulfur; Synthetic methods; SULFOXIMINES; ORGANIC-CHEMICALS; Sulfonimidamides; ARYLATION; EFFICIENT SYNTHESIS; AMIDATION; BOND FORMATION; C-H activation; DIRECT AMINATION; C-N coupling; BENZOXAZOLES; Synthetic methods; ARYL; Sulfur; Copper; Alkynes; INSIGHTS
• ISSN: 1434-193X; 1099-0690
• DOI: 10.1002/ejoc.201500239

We report a mild and efficient Cu(OAc)2‐catalysed protocol for the oxidative C–N cross‐coupling of terminal alkynes and N‐deprotected sulfonimidamides. The reaction leads to hitherto unknown N‐alkynylated sulfonimidamides. Furthermore, we found that the synthesised N‐alkynylated sulfonimidamides could undergo silica‐gel‐mediated hydrolysis to give the corresponding N‐acyl‐sulfonimidamides, as well as borane–dimethyl sulfide‐mediated reduction to give the corresponding N‐alkylated sulfonimidamides. N‐Alkynylated sulfonimidamides have been synthesised through the CuII‐catalysed N–H/C–H activation reaction of N‐deprotected sulfonimidamides and terminal alkynes. The resulting N‐alkynylated sulfonimidamides react with SiO2 or BH3·SMe2 to give the corresponding carbonyl or alkyl derivative, respectively.