Naphthalene-1,8-diamido dan derivative Ar Ph

2-Methyl-5-phenylpentyl benzyl(phenyl]carbamate (Rj,nq,i = Me, X = Br, R ai yi = CHjCHjCHjPh) 

Part 1 (Formation and activation of B-alkyl-(9-BBN) reagents) To a suspension of 9-BBN dimer (4.6 g, 18.8 mmol, 1.0 equiv) in i-Pr20 (10 ml) was added allylbenzene (4.4 g, 5.0 ml, 1.0 equiv) in a N2-filled glovebox. The reaction mixture was then heated at 60 °C for 1.5 h outside of the glovebox, cooled down to room temperature, and diluted with i-Pr20 to produce a 1.5 M solution (total volume 25 ml) of the alkylborane reagent. 

To activate the alkylborane reagent, a solution of the alkylborane reagent (1.5 M, 670 pi, 1.0 mmol, 2.0 equiv relative to the section below) was added to a slurry of KOt-Bu (78.5 mg, 0.70 mmol, 1.4 equiv relative to the section below) and hexanol (92.0 mg, 113 pi, 0.90 mmol, 1.8 equiv relative to the section below), which was vigorously stirred for 45 min at room temperature before being immediately used in the cross-coupling reactions. 

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