Scheme 1.

Scope for the Synthesis of Naphthalenes

Reaction conditions: Method A: 1 or 4 (0.2 mmol), JohnPhosAuSbF₆ (0.01 mmol) in DCE (1,2-dichloroethane, 2.0 mL) at 25°C,12 h, and yields are given in isolated yields. Method B: 14 (0.2 mmol), Ar-H (0.3 mmol), JohnPhosAuSbF₆ (0.01 mmol) in DCE (1,2-dichloroethane, 2.0 mL) at 60°C, 3 h, and yields are given in isolated yields.

The reaction was conducted on a 4.0-mmol scale.

(A) Synthesis of 2,3-disubstituted naphthalenes.

(B) Synthesis of 1,2,3-trisubstituted naphthalenes.

(C) Synthesis of 1,2,3,4-tetrasubstituted naphthalenes.