Pd(0)-catalyzed selective [2+2+2] cycloaddition of dimethyl nona-2,7-diyne-1,9-dioate derivatives with dimethyl acetylenedicarboxylate

被引：51

作者：

Yamamoto, Y

Nagata, A

Itoh, K ^{[1
]}

机构：

[1] Nagoya Univ, Grad Sch Engn, Dept Appl Chem, Chikusa Ku, Nagoya, Aichi 4648603, Japan

[2] Nagoya Univ, Grad Sch Engn, Dept Mol Design & Engn, Chikusa Ku, Nagoya, Aichi 4648603, Japan

来源：

TETRAHEDRON LETTERS | 1999年 / 40卷 / 27期

关键词：

palladium catalyst; cycloadditions; alkynes; bicyclic aromatic compounds;

D O I：

10.1016/S0040-4039(99)00927-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

In the presence of 2.5 mol % of Pd-2(dba)(3) and 5 mol % of PPh3, nearly equimolar amounts of dimethyl nona-2,7-diyne-1,9-dioate derivatives and dimethyl acetylenedicarboxylate (DMAD) were reacted in toluene at 110 degrees C to give indan, phthalin, and isoindoline derivatives selectively in moderate to good yields. The competing home-couplings of both the diynediesters and DMAD were completely suppressed. The ester groups on the alkyne terminus plays an important role; the corresponding diynediketone and diynemonoester gave unsatisfactory results. The present Pd(0)-catalyzed cyclotrimerization was further extended to the intramolecular [2 + 2 + 2] cycloaddition of a triynediester. (C) 1999 Elsevier Science Ltd. All rights reserved.

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页码：5035 / 5038

页数：4

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