3451-01-2Relevant articles and documents
1,2-Alkylarylation of Activated Alkenes with Two C-H Bonds by Using Visible-Light Catalysis
Zhang, Jia-Ling,Liu, Yu,Song, Ren-Jie,Jiang, Guo-Fang,Li, Jin-Heng
, p. 1031 - 1035 (2014)
A new visible-light promoted strategy for the difunctionalization of activated alkenes with two C-H bonds has been developed. In the presence of [Ru(bpy)3Cl2], 4-MeOC6H4N 2BF4, Na2CO3 and 36 W compact fluorescent light, a variety of N-arylacrylamides underwent the 1,2-alkylarylation reaction with acetonitrile or acetone to give the corresponding functionalized oxindoles in moderate to good yields. Georg Thieme Verlag Stuttgart New York.
Radical cascade cyanomethylation of activated alkenes to construct cyano substituted oxindoles
Li, Juan,Wang, Zhigang,Wu, Ningjie,Gao, Ge,You, Jingsong
, p. 15049 - 15051 (2014)
The cyanomethyl radical was easily generated from acetonitrile by using DTBP, which was applied to a cascade alkene addition and cyclization reaction to construct useful oxindole derivatives. This protocol features simple manipulation, cheap reagents and a broad substrate scope. In addition, nitro substituted oxindoles were also synthesized for the first time. This journal is
Azo-compound-mediated cyanoalkylation of alkenes by copper catalysis: General access to cyano-substituted oxindoles
Tang, Shi,Zhou, Dong,Li, Zhi-Hao,Fu, Mei-Jun,Jie, Li,Sheng, Rui-Long,Li, Shu-Hua
, p. 1567 - 1580 (2015)
Abstract A practical and highly efficient azo-compound-mediated/ promoted radical cyanoalkylation of activated alkenes by copper catalysis was developed, which allowed for general synthesis of oxindoles bearing various nitrile moieties, especially the rarely reported 3° nitrile moiety via cascade radical addition/C(sp2)-H cyclization. This protocol demonstrates that DIAD served for a new promoter instead of usual Ag salts or bases in the C(sp3)-H functionalization of acetonitrile for the first time. The use of readily available AIBN and beyond as the radical sources, and inexpensive copper as the catalyst, as well as the simplicity of operation and handling, make this protocol an attractive access to therapeutically important cyano-substituted oxindoles.
DIAD as a promoter for cyanomethylation of alkenes by Cu catalysis
Tang, Shi,Li, Shu-Hua,Li, Zhi-Hao,Zhou, Dong,Sheng, Rui-Long
, p. 1423 - 1426 (2015)
A novel and practical DIAD-promoted oxidative cyanomethylation of alkenes with acetonitrile by copper catalysis was developed, in which oxindoles bearing a nitrile moiety at the 3-position were synthesized efficiently via dual C-H bond cleavage of an arene and acetonitrile. This protocol demonstrated that DIAD served as a new promoter instead of commonly encountered AgF or base for the Csp3-H functionalization of acetonitrile for the first time.
Heterogeneous photocatalytic cyanomethylarylation of alkenes with acetonitrile: Synthesis of diverse nitrogenous heterocyclic compounds
Pan, Guanglong,Yang, Qian,Wang, Wentao,Tang, Yurong,Cai, Yunfei
supporting information, p. 1171 - 1180 (2021/05/27)
A visible light-mediated heterogeneous photocatalytic cyanomethylarylation of alkenes with acetonitrile has been established using K-modified carbon nitride (CN-K) as a recyclable semiconductor photocatalyst. This protocol, employing readily accessible al
Fe-promoted radical cyanomethylation/arylation of arylacrylamides to access oxindoles via cleavage of the sp3 C-H of acetonitrile and the sp2 C-H of the phenyl group
Pan, Changduo,Zhang, Honglin,Zhu, Chengjian
supporting information, p. 361 - 364 (2015/02/05)
Radical cyanomethylation/arylation of arylacrylamides to access oxindoles with acetonitrile as the radical precursor is described. This reaction involves dual C-H bond functionalization, including the sp3 C-H of acetonitrile and the sp2/s
