Highly cis- and trans-selective alkyl radical addition to α-methylene-γ-phenyl-γ-butyrolactams

2009 ◽  
Vol 50 (12) ◽  
pp. 1301-1302 ◽  
Author(s):  
Tomoko Yajima ◽  
Masako Hamano ◽  
Hajime Nagano
Keyword(s):  
Alkyl Radical ◽  
Radical Addition ◽  
Cis And Trans

scholarly journals One-Pot Four-Component Reaction: Aqueous TiCl3/PhN+2-Mediated Alkyl Radical Addition to Imines Generated in situ.

ChemInform ◽  
2005 ◽  
Vol 36 (27) ◽  
Author(s):  
Rosalba Cannella ◽  
Angelo Clerici ◽  
Nadia Pastori ◽  
Eva Regolini ◽  
Ombretta Porta
Keyword(s):  
Alkyl Radical ◽  
Radical Addition ◽  
One Pot

scholarly journals Controlling alkyne reactivity by means of a copper-catalyzed radical reaction system for the synthesis of functionalized quaternary carbons

2020 ◽  
Vol 16 ◽  
pp. 502-508
Author(s):  
Goki Hirata ◽  
Yu Yamane ◽  
Naoya Tsubaki ◽  
Reina Hara ◽  
Takashi Nishikata
Keyword(s):  
Alkyl Radical ◽  
Copper Catalyst ◽  
Radical Reaction ◽  
Reaction System ◽  
Radical Addition ◽  
Terminal Alkyne ◽  
Multiple Bonds ◽  
Complex Molecules ◽  
Reaction Patterns ◽  
Tertiary Alkyl

A terminal alkyne is one of the most useful reactants for the synthesis of alkyne and alkene derivatives. Because an alkyne undergoes addition reaction at a C–C triple bond or cross-coupling at a terminal C–H bond. Combining those reaction patterns could realize a new reaction methodology to synthesize complex molecules including C–C multiple bonds. In this report, we found that the reaction of 3 equivalents of terminal alkyne 1 (aryl substituted alkyne) and an α-bromocarbonyl compound 2 (tertiary alkyl radical precursor) undergoes tandem alkyl radical addition/Sonogashira coupling to produce 1,3-enyne compound 3 possessing a quaternary carbon in the presence of a copper catalyst. Moreover, the reaction of α-bromocarbonyl compound 2 and an alkyne 4 possessing a carboxamide moiety undergoes tandem alkyl radical addition/C–H coupling to produce indolinone derivative 5.

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