28080-86-6

Usage

Synthesis Reference(s)

The Journal of Organic Chemistry, 58, p. 4866, 1993 DOI: 10.1021/jo00070a022

InChI:InChI=1/C12H18/c1-4-12(2,3)10-11-8-6-5-7-9-11/h5-9H,4,10H2,1-3H3

Upstream product

• 33214-68-5 3,3-dimethyl-4-phenyl-butan-1-ol 
• 105474-54-2 (4-bromo-2,2-dimethyl-butyl)-benzene 
• 594-36-5 2-methyl-2-butylchloride 
• 6921-34-2 benzylmagnesium chloride 
• 66390-59-8 α-t-amylbenzyl alcohol 
• 917-64-6 methyl magnesium iodide 
• 40548-64-9 3-iodo-2,2-dimethyl-1-phenylpropane 
• 69113-05-9 1-<(1,1-dimethylethyl)sulphonyl>-2-methylbenzene 
• 102211-93-8 2,4-xylyl tert-amyl sulfone 
• 676-58-4 methylmagnesium chloride 
• 75-16-1 methylmagnesium bromide 
• 6802-75-1 diethyl isopropylidenemalonate 
• 5415-86-1 diethyl 2-(2-methyl-1-phenylpropan-2-yl)malonate 
• 78-78-4 methylbutane 

Relevant academic research and scientific papers

Nickel-Mediated Cross-Coupling of Unactivated Neopentyl Iodides with Organozincs

(dppf)NiCl2 catalyzes the cross-coupling of unactivated primary neopentyl iodides with diorganozinc reagents.The zinc nucleophiles are formed by the treatment of ZnCl2*dioxane with 2 mol equiv of a Grignard reagent in an etheral solvent.The cross-coupling works optimally for diorganozincs formed from aryl chlorides or CH3MgCl.Use of aryl bromides can cause reduction and/or reductive dimerization of the electrophile.The analogous reaction with (CH3)2CuMgCl in either the presence or the absence of Group 10 metal catalysts failed to afford reasonable yields of cross-coupled products.The diorganozinc methodology overcomes many of the side reactions observed with the (dppf)NiCl2-mediated cross-coupling of Grignard reagents.

Nickel-catalyzed cross-coupling of unactivated neopentyl iodides with Grignard reagents

Primary neopentyl iodides react with aryl Grignard reagents in the presence of 10 mol% (dppf)NiCl2 to give the cross-coupled product.

Rearrangement of Benzylically Lithiated Methylaryl Alkyl Sulfones

Lithiathion of appropriate methylaryl alkyl sulfones is followed by migration of the alkyl group from sulfur to the benzylic carbon.Product studies, relative reactivities, and crossover experiments are consistent with a radical-radical anion chain process for this rearrangement.