Palladium-Catalyzed Double Cross-Coupling Reaction of vic-Diborylalkenes and -arenes with vic-Bromo(bromomethyl)arenes

Abstract

Efficient annulation of vic-diborylalkenes and -arenes with vic-bromo(bromomethyl)arenes has been achieved, using Pd(PPh₃)₄ as a catalyst in the presence of Cs₂CO₃ and water in THF at 60 ˚C, giving rise to the corresponding indene and fluorene derivatives in good to high yields.

Key words

annulations - arenes - boron - bromine - cross-coupling

References and Notes

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For details, see Supporting Information.

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Crystallographic Data for 4a
C₂₇H₂₈BBrO₂, M = 475.21, triclinic, a = 9.9742(7), b = 10.2322(7), c = 13.9705(9) Å, α = 86.0320(10), β = 69.5850(10), γ = 64.4340(10)˚, U = 1199.82(14)
Å^³, T = 300 K, space group P1, Z = 2, 6571 reflections collected, unique 4380 (R _int = 0.0142), final R indices [I > 2σ(I)] R1 = 0.0558, wR2 = 0.1530. CCDC-737101 contains the supplementary crystallographic data.

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In some cases, slight modification of a base was necessary for attaining a good yield of the product. On the other hand, the reaction of 1-bromo-2-(1-bromoethyl)benzene with 1a failed so far although various bases and conditions were screened.