Details

Autor(en) / Beteiligte

• Shu, Xing-Zhong
• Xia, Xiao-Feng
• Yang, Yan-Fang
• Ji, Ke-Gong
• Liu, Xue-Yuan
• Liang, Yong-Min

Titel

Selective functionalization of sp(3) C-H bonds adjacent to nitrogen using (diacetoxyiodo)benzene (DIB)

Ist Teil von

• Journal of organic chemistry, 2009-10, Vol.74 (19), p.7464-7469

Ort / Verlag

United States

Erscheinungsjahr

2009

Link zum Volltext

Quelle

Alma/SFX Local Collection

Beschreibungen/Notizen

• A PhI(OAc)(2) mediated selective functionalization of sp(3) C-H bonds adjacent to a nitrogen atom has been reported. When piperidine derivates were used, direct diacetoxylation of alpha and beta sp(3) C-H adjacent to a nitrogen atom were observed to afford various cis-2,3-diacetoxylated piperidines. On the other hand, tetrahydroisoquinoline derivatives gave various alpha-C-H functionalized products in the presence of PhI(OAc)(2). Nitroalkanes, dialkyl malonates, and beta-keto ester are active participants in this coupling reaction. Meanwhile, alpha-amino nitriles can also be obtained by oxidative coupling of amines with malononitrile.