Metal‐free Radical Cyclization of Olefinic 1, 3‐Dicarbonyls and Olefinic Amides with Nitrile C(sp3)−H Bonds in Aqueous Media. Issue 12 (26th October 2021)

• Record Type: Journal Article
• Authors: Qin, Fu‐Hua; Wang, Hui‐Zhi; Cao, Ting‐Ting; Liu, Qi‐Li; Xu, Qing; Zheng, Hongxing; Zhu, Meiling; Li, Ting; Liu, Yi‐Lin; Wei, Wen‐Ting
• Is Part Of: Asian journal of organic chemistry. Volume 10:Issue 12(2021)
• Page Start: 3380
• Page End: 3383
• Publication Date: 2021-10-26
• Subjects: Aqueous media -- Base-free -- Green synthesis -- Metal-free -- Radical C(sp3)−H functionalization; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; 547.005
• DOI: 10.1002/ajoc.202100586
• Languages: English
• ISSNs: 2193-5807

Abstract

Abstract: A radical cyclization of olefinic 1, 3‐dicarbonyls and olefinic amides with nitrile C(sp 3 )−H bonds for the preparation of valuable 2, 3‐dihydrofurans and benzoxazines have been developed. This protocol can be conducted at metal‐ and base‐free conditions in aqueous media with moderate to good yields. Moreover, the practicality of this strategy is further highlighted by gram‐scale reactions. The mechanistic investigation reveals that the transformation is initiated by in‐situ formed cyanomethyl radical. Abstract : A radical cyclization of olefinic 1, 3‐dicarbonyls and olefinic amides with nitrile C(sp 3 )−H bonds for the preparation of valuable 2, 3‐dihydrofurans and benzoxazines has been developed. This protocol can be conducted at metal‐ and base‐free conditions in aqueous media with moderate to good yields.