Propargylic and Allenic Carbocycle Synthesis through Palladium-Catalyzed Dearomatization Reaction

被引：34

作者：

Peng, Bo ^{[1
]}

Feng, Xiujuan ^{[1
]}

Zhang, Xin ^{[2
]}

Zhang, Sheng ^{[1
]}

Bao, Ming ^{[1
]}

机构：

[1] Dalian Univ Technol, State Key Lab Fine Chem, Dalian 116012, Peoples R China

[2] Dalian Univ Technol, Sch Environm Sci & Technol, Dalian 116023, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2010年 / 75卷 / 08期

基金：

中国国家自然科学基金;

关键词：

METAL-MEDIATED DEAROMATIZATION; MONOSUBSTITUTED BENZENES; ASYMMETRIC ALLYLATION; DE-AROMATIZATION; COMPLEXES; DERIVATIVES; PHOTOCYCLOADDITION; REARRANGEMENT; CYCLIZATION; MECHANISM;

D O I：

10.1021/jo100211d

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The dearomatization reaction of benzylic chlorides (1a-k), chloromethylnaphthalenes (1l-r), and naphthalene allyl chlorides (3a-d) with allenyltributyltin proceeded smoothly in the presence of Pd(PPh(3))(4) catalyst at room temperature to give the corresponding propargylated and/or allenylated dearomatization products (5, 5'; 6, 6'; and 7, respectively) in high to fair yields. The reaction of 1a-k proceeded smoothly in the presence of TBAF, whereas it was not necessary to use TBAF as an additive in the reactions of 1l-k and 3a-d. These reactions provided a new and efficient method for the synthesis of propargylic and allenic carbocycles.

引用

页码：2619 / 2627

页数：9

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