Chelation-assisted nucleophilic aromatic substitution of 2-sulfonyl-substituted 1-methoxynaphthalenes by Grignard reagents: factors determining the activating ability of the 2-sulfonyl substituents 1,2

Abstract

1-Methoxynaphthalenes 3–7 having sulfonyl substituents SO₂R (R = Me, Prⁱ, Bu^t, OPh and [upper bond 1 start]N[CH₂]₃C[upper bond 1 end]H₂) at the 2-position undergo displacement of the 1-methoxy group on treatment with the Grignard reagents 8a–d by a chelation-assisted conjugate addition–elimination process. Activating ability of these sulfonyl groups for the apparent nucleophilic aromatic substitution is compared with that of an ester group, isopropoxycarbonyl, and a sulfinyl group, tert-butylsulfinyl, and found to fall roughly in the order CO₂Prⁱ > SO₂OPh > SO₂[upper bond 1 start]N[CH₂]₃C [upper bond 1 end]H₂ ⩾ SO₂ Alkyl ⪢ SOBu^t . The activation order is interpreted as being the outcome of a balance between the electron-withdrawing strength of the 2-substituents and the steric hindrance caused by the Grignard reagents 8a–d on approach to the substrates 1-methoxynaphthalenes 1–7. Asymmetric binaphthyl coupling by reaction of the chiral sulfamoyl-substituted naphthalene 20 with 1-naphthyl Grignard reagents 8d,e is also reported.

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