108871-76-7Relevant academic research and scientific papers
N-Heterocyclic Carbene-Catalyzed Truce-Smiles Rearrangement of N-Arylacrylamides via the Cleavage of Unactivated C(aryl)-N Bonds
Yasui, Kosuke,Kamitani, Miharu,Fujimoto, Hayato,Tobisu, Mamoru
supporting information, p. 1572 - 1576 (2021/03/03)
We report on the N-heterocyclic carbene (NHC)-catalyzed Truce-Smiles rearrangement of aniline derivatives, in which an unactivated C(aryl)-N bond is cleaved, leading to the formation of a new C(aryl)-C bond. The key to the success of this reaction is the
Nickel-Catalyzed Transformation of Diazoacetates to Alkyl Radicals Using Alcohol as a Hydrogen Source
Zhao, Jingjing,Li, Pan,Xu, Yaohua,Shi, Yixin,Li, Fuwei
supporting information, p. 9386 - 9390 (2019/11/28)
A nickel-catalyzed transformation of diazoacetates to α-carbonyl methylene radicals has been disclosed in the presence of hyperoxide using ethanol as a hydrogen source and solvent. This strategy is successfully applied in the formation of indolin-2-ones or 1,4-dicarbonyl compounds from acrylamides or enamides in moderate to good yields. These reactions undergo radical addition onto C-C double bonds followed by a cyclization/oxidation or an oxidation/hydrolysis process, respectively.
High-valent palladium-promoted formal Wagner-Meerwein rearrangement
Wu, Hongmiao,Yang, Bin,Zhu, Lin,Lu, Ronghua,Li, Guigen,Lu, Hongjian
supporting information, p. 5804 - 5807 (2016/11/29)
An oxy-palladation, formal Wagner-Meerwein rearrangement and fluorination cascade has been established for generating fluorinated oxazolidine-2,4-diones and oxazolidin-2-ones. The reaction has a broad substrate scope in which both aryl and alkyl groups can be utilized as efficient migrating groups. Experimental evidence suggests that the reaction is initiated by anti-oxy-palladation of the olefin, followed by oxidative generation of an alkyl PdIV intermediate and a concerted migration-fluorination.
Metal-free nitro-carbocyclization of activated alkenes: A direct approach to synthesize oxindoles by cascade C-N and C-C bond formation
Shen, Tao,Yuan, Yizhi,Jiao, Ning
supporting information, p. 554 - 556 (2014/01/06)
A novel and direct metal-free nitro-carbocyclization of activated alkenes leading to valuable nitro-containing oxindoles via cascade C-N and C-C bond formation has been developed. The mechanistic study indicates that the initial NO and NO2 radical addition and the following C-H functionalization processes are involved in this transformation. The Royal Society of Chemistry 2014.
Iron-catalyzed aerobic difunctionalization of alkenes: A highly efficient approach to construct oxindoles by C-S and C-C bond formation
Shen, Tao,Yuan, Yizhi,Song, Song,Jiao, Ning
supporting information, p. 4115 - 4118 (2014/04/03)
A novel iron-catalyzed efficient approach to construct sulfone-containing oxindoles, which play important roles in the structural library design and drug discovery, has been developed. The use of readily available benzenesulfinic acids, an inexpensive iron salt as the catalyst, and air as the oxidant makes this sulfur incorporation protocol very efficient and practical. This journal is the Partner Organisations 2014.
Ag-promoted azido-carbocyclization of activated alkenes via C - H bond cleavage
Yuan, Yizhi,Shen, Tao,Wang, Kui,Jiao, Ning
supporting information, p. 2932 - 2935 (2014/01/06)
A sliver of silver: An efficient silver-promoted azido-carbocyclization of activated alkenes via a radical pathway has been developed. Azido oxindoles, which hold great potential for subsequent transformation of the azido unit, are efficiently constructed by this protocol. Radical addition and C - H functionalization processes are involved in this transformation with the formation of C - N and C - C bonds. Silver is observed to promote the single-electron oxidation process. Copyright
Palladium-catalyzed oxidative arylalkylation of activated alkenes: Dual C-H bond cleavage of an arene and acetonitrile
Wu, Tao,Mu, Xin,Liu, Guosheng
supporting information; scheme or table, p. 12578 - 12581 (2012/02/04)
Not one but two: The title reaction proceeds through the dual C-H bond cleavage of both aniline and acetonitrile (see scheme). The reaction affords a variety of cyano-bearing indolinones in excellent yield. Mechanistic studies demonstrate that this reaction involves a fast arylation of the olefin and a rate-determining C-H activation of the acetonitrile. Copyright
