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

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

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....

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Veröffentlicht in:Journal of organic chemistry 2009-10, Vol.74 (19), p.7464-7469
Hauptverfasser: Shu, Xing-Zhong, Xia, Xiao-Feng, Yang, Yan-Fang, Ji, Ke-Gong, Liu, Xue-Yuan, Liang, Yong-Min
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container_end_page 7469
container_issue 19
container_start_page 7464
container_title Journal of organic chemistry
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creator Shu, Xing-Zhong
Xia, Xiao-Feng
Yang, Yan-Fang
Ji, Ke-Gong
Liu, Xue-Yuan
Liang, Yong-Min
description 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.
doi_str_mv 10.1021/jo901583r
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title Selective functionalization of sp(3) C-H bonds adjacent to nitrogen using (diacetoxyiodo)benzene (DIB)
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