14248-19-2

Upstream product

• 100-39-0 benzyl bromide 
• 5669-14-7 2,2-dimethyl-3-phenylpropanoic acid 
• 100-44-7 benzyl chloride 
• 14248-22-7 methyl 2,2-dimethyl-3-phenylpropionate 
• 13351-61-6 2,2-dimethyl-3-phenyl-1-propanol 
• 98-59-9 p-toluenesulfonyl chloride 

Downstream Products

• 40548-64-9 3-iodo-2,2-dimethyl-1-phenylpropane 
• 5916-22-3 p-methyl-β,β-dimethylstyrene 
• 644-08-6 4-Methylbiphenyl 
• 53040-92-9 4-(4-tolyl)anisole 
• 27331-34-6 1-(4-methylphenyl)naphthalene 
• 7653-94-3 1,1-dimethyl-2-phenylcyclopropane 

Relevant academic research and scientific papers

Nickel(0)/NaHMDS adduct-mediated intramolecular alkylation of unactivated arenes via a homolytic aromatic substitution mechanism

A variety of polycycles can be synthesized via an intramolecular alkylation cyclization promoted by Ni(PPh3)4 and NaHMDS. Mechanistic investigations support the catalytic nature of Ni0 in the course of TEMPO scavenging experiments and its association with the substrate and NaHMDS to form an adduct by DOSY NMR.

Nickel(0)-catalyzed cross-coupling of alkyl arenesulfonates with aryl Grignard reagents

The nickel-catalyzed cross-coupling reactions of neopentyl arenesulfonates with arylmagnesium bromides, involving nucleophilic aromatic substitution of alkyloxysulfonyl groups by aryl nucleophiles, take place in high yields. Optimal efficiencies are obtained by adding 3 + 2 equiv of the Grignard reagent to a mixture of dppfNiCl2 and the sulfonate in refluxing THF. Neopentyl arenesulfonates are useful sources of the electrophilic aryl groups in these transition metal-catalyzed cross-coupling reactions. Aryl sulfonates are inappropriate due to their ambident reactivity under the reaction conditions. This new cross-coupling reaction can be used for the creative elimination of alkyloxysulfonyl groups from aromatic compounds and for the preparation of unsymmetric terphenyls and oligophenyls.