Chemistry Letters

Synthesis of ortho-Acylbenzylboronates via Cross-Coupling Reaction of (Dialkoxyboryl) methylzinc Reagents with Haloarenes. A Stable ortho-Quinodimethane …

G Kanai, N Miyaura, A Suzuki

Index: Kanai, Gen; Miyaura, Norio; Suzuki, Akira Chemistry Letters, 1993 , # 5 p. 845 - 848

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Citation Number: 19

Abstract

The cross-coupling reaction of IZnCH 2 B (OCMe 2) with iodoarenes in the presence of PdCl 2 (PPh 3) 2 produces the corresponding benzylic boronates in high yields. Among them, the benzylic boronates having an acyl group at the ortho position readily undergo the 1, 5- rearrangement to the carbonyl oxygen producing the o-quinodimethane derivatives under thermal or photochemical conditions. The reaction provides benzo-fused cycloalkanes by ...