title: Selective functionalization of sp(3) C-H bonds adjacent to nitrogen using (diacetoxyiodo)benzene (DIB).
abstract: 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.
authors.affiliation: State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, PR China.
authors.forename: Xing-Zhong
authors.initials: XZ
authors.lastname: Shu
authors.forename: Xiao-Feng
authors.initials: XF
authors.lastname: Xia
authors.forename: Yan-Fang
authors.initials: YF
authors.lastname: Yang
authors.forename: Ke-Gong
authors.initials: KG
authors.lastname: Ji
authors.forename: Xue-Yuan
authors.initials: XY
authors.lastname: Liu
authors.forename: Yong-Min
authors.initials: YM
authors.lastname: Liang