15232-91-4

Usage

InChI:InChI=1/C10H18/c1-3-9(2)10-7-5-4-6-8-10/h5,7,9-10H,3-4,6,8H2,1-2H3

Upstream product

• 822-67-3 Cyclohex-2-enol 
• 671795-46-3 sec-butylmagnesium bromide 
• 102853-22-5 cyclohex-2-en-1-yl 2,4,6-trimethylbenzoate 

Relevant academic research and scientific papers

Alkylation of Allylic Derivatives. 11. Copper(I)-Catalyzed Cross Coupling of Allylic Carboxylates with Grignard Reagents

Reactions of allylic carboxylates with Grignard reagents containing catalytic amounts (1-10 mol percent) of cuprous salts give high yields of cross-coupled products.With alkyl Grignard reagents, regiochemistry can be controlled by choice of cuprous salt.With cuprous halides, little regiospecificity is observed.There is a small excess of γ-coupling in unbiased systems such as 5-methyl-2-cyclohexenyl (1), 2-cyclohexenyl (3), and β-phenylallyl (5) carboxylates.With CuCN, complete regiospecificity (exclusive γ-coupling) is observed with all alkyl Grignard reagents in unbiased systems, and with n-butylmagnesium halide >97percent γ-coupling results with α-methyl-γ-phenylallyl pivalate (7-OPiv) which is biased in favour of coupling at the α-position.In sharp contrast to alkyl Grignard reagents, phenyl and vinyl Grignard reagents containing CuCN show no regiospecificity.