3412-44-0Relevant articles and documents
Shapiro
, p. 345 (1968)
Nickel-Catalyzed C-Br/C-H Bis-phenylation of Methyl 4-Bromocrotonate: A Stereoselective Entry to Methyl (E)-3,4-Diphenylbut-2-enoate
Funicello, Maria,Chiummiento, Lucia,Lupattelli, Paolo,Tramutola, Francesco
, p. 1799 - 1806 (2015)
A method for C-Br/C-H bis-phenylation of methyl 4-bromocrotonate via nickel-catalyzed cross-coupling reaction has been developed. This protocol involves commercially available catalyst components and furnishes a suitable doubly phenylated building block.
Vinylation of Benzylic Amines via C-N Bond Functionalization of Benzylic Pyridinium Salts
Guan, Weiye,Liao, Jennie,Watson, Mary P.
, p. 3231 - 3237 (2018)
Cross-couplings of benzylic pyridinium salts and vinylboronic acids or esters have been developed. Via benzylic pyridinium intermediates, benzylic amines can be engaged in these cross-couplings through C-N bond functionalization. This method boasts mild reaction conditions and excellent tolerance for heteroaryl substituents and a range of functional groups.
Palladacycle-Catalyzed Regioselective Heck Reaction Using Diaryliodonium Triflates and Aryl Iodides
Hou, Cheng,Lei, Lu,Liang, Cui,Mo, Dong-Liang,Wang, Zhi-Xin,Zou, Pei-Sen
supporting information, p. 663 - 667 (2022/01/28)
We describe a P-containing palladacycle-catalyzed regioselective Heck reaction of 2,3-dihydrofuran with diaryliodonium salts and aryl iodides to afford 2-aryl-2,5-dihydrofurans and 2-aryl-2,3-dihydrofurans, respectively, in good yields. Mechanistic studie
Nickel-Catalyzed Electrochemical C(sp3)?C(sp2) Cross-Coupling Reactions of Benzyl Trifluoroborate and Organic Halides**
Luo, Jian,Hu, Bo,Wu, Wenda,Hu, Maowei,Liu, T. Leo
supporting information, p. 6107 - 6116 (2021/02/01)
Reported here is the redox neutral electrochemical C(sp2)?C(sp3) cross-coupling reaction of bench-stable aryl halides or β-bromostyrene (electrophiles) and benzylic trifluoroborates (nucleophiles) using nonprecious, bench-stable NiCl2?glyme/polypyridine catalysts in an undivided cell configuration under ambient conditions. The broad reaction scope and good yields of the Ni-catalyzed electrochemical coupling reactions were confirmed by 50 examples of aryl/β-styrenyl chloride/bromide and benzylic trifluoroborates. Potential applications were demonstrated by electrosynthesis and late-stage functionalization of pharmaceuticals and natural amino acid modification, and three reactions were run on gram-scale in a flow-cell electrolyzer. The electrochemical C?C cross-coupling reactions proceed through an unconventional radical transmetalation mechanism. This method is highly productive and expected to find wide-spread applications in organic synthesis.