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Synlett 2009(19): 3147-3150  
DOI: 10.1055/s-0029-1218341
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

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

Masaki Shimizu*, Yosuke Tomioka, Ikuhiro Nagao, Tamejiro Hiyama
Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Kyoto University Katsura, Nishikyo-ku, Kyoto 615-8510, Japan
Fax: +81(75)3832445; e-Mail: m.shimizu@hs2.ecs.kyoto-u.ac.jp;
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Publikationsverlauf

Received 19 September 2009
Publikationsdatum:
03. November 2009 (online)

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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

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7

For details, see Supporting Information.

8

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)
ų, 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.

10

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.