(Diacetoxyiodo)benzene‐Mediated Oxygenation of Benzylic C(sp3)–H Bonds with N‐Hydroxyamides at Room Temperature. Issue 8 (5th February 2015)

• Record Type: Journal Article
• Authors: Qian, Peng‐Cheng; Liu, Yu; Song, Ren‐Jie; Hu, Ming; Yang, Xu‐Heng; Xiang, Jian‐Nan; Li, Jin‐Heng
• Is Part Of: European journal of organic chemistry. Issue 8(2015)
• Page Start: 1680
• Page End: 1684
• Publication Date: 2015-02-05
• Subjects: Oxidation -- N‐Hydroxyamides -- Cross‐coupling -- Acetamides -- Synthetic methods; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201403616
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract: A new, metal‐free method for the formation of C(sp 3 )–O bonds was established by PhI(OAc)2 ‐mediated oxygenation of benzylic C(sp 3 )–H bonds with N ‐hydroxyamides at room temperature, in which the C(sp 3 )–H oxidation is activated by a polyflurophenylamide group. Abstract : A metal‐free, room temperature route to construct C(sp 3 )–O bonds is described by PhI(OAc)2 ‐mediated oxygenation of a benzylic C(sp 3 )–H bond with the O–H bond in N ‐hydroxyamides. This method is facilitated by an electron‐withdrawing amide group, and provides a transition‐metal‐free room temperature alternative for the formation of C(sp 3 )–O bonds with highly functional group compatibility.