Nickel-Phosphine Complex-Catalyzed Grignard Coupling. I. Cross-Coupling of Alkyl, Aryl, and Alkenyl Grignard Reagents with Aryl and Alkenyl Halides: General Scope and Limitations
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چکیده
منابع مشابه
Single electron transfer-induced cross-coupling reaction of alkenyl halides with aryl Grignard reagents.
Alkenyl halides were found to undergo coupling with aryl Grignard reagents to give the corresponding styrene derivatives in a stereo-retained manner. The cross-coupling reaction is considered to proceed through a single electron transfer mechanism.
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The use of transition-metal catalysis to form new C C bonds is an important tool in organic synthesis. Palladiumand nickel-catalyzed C C bond-forming reactions have been extensively explored and are well understood. The use of iron as the catalyst has gained much less attention, despite the innovative work of Kochi et al. in the 1970s. Recently, several groups have turned their attention toward...
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Iron nanoparticles, either formed in situ stabilized by 1,6-bis(diphenylphosphino)hexane or polyethylene glycol (PEG), or preformed stabilized by PEG, are excellent catalysts for the cross-coupling of aryl Grignard reagents with primary and secondary alkyl halides bearing beta-hydrogens and they also prove effective in a tandem cyclization/cross-coupling reaction.
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Alkenyl triflates in combination with Co(acac)(3) as a catalyst were found to be excellent coupling partners of alkynyl Grignard reagents, where no special additives (even a phosphine ligand) but a common solvent, THF, are required to obtain variously substituted enynes.
متن کاملMild and phosphine-free iron-catalyzed cross-coupling of nonactivated secondary alkyl halides with alkynyl Grignard reagents.
A simple protocol for iron-catalyzed cross-coupling of nonactivated secondary alkyl bromides and iodides with alkynyl Grignard reagents at room temperature has been developed. A wide range of secondary alkyl halides and terminal alkynes are tolerated to afford the substituted alkynes in good yields. A slight modification of the reaction protocol also allows for cross-coupling with a variety of ...
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ژورنال
عنوان ژورنال: Bulletin of the Chemical Society of Japan
سال: 1976
ISSN: 0009-2673,1348-0634
DOI: 10.1246/bcsj.49.1958