Gold catalysis: Experimental mechanistic insights into the anellation of phenols with 1,3-dienes

被引：5

作者：

Bay, Sarah ^{[1
]}

Englert, Alexandra ^{[1
]}

Nalivela, Kumara Swamy ^{[1
]}

Hashmi, A. Stephen K. ^{[1
,2
]}

Larsen, Mie Hojer ^{[1
]}

机构：

[1] Heidelberg Univ, Inst Organ Chem, D-69120 Heidelberg, Germany

[2] King Abdulaziz Univ, Dept Chem, Fac Sci, Jeddah 21589, Saudi Arabia

来源：

JOURNAL OF ORGANOMETALLIC CHEMISTRY | 2015年 / 795卷

关键词：

1,3-Dienes; Gold; Heterocycles; Phenols; Reaction mechanisms; C-C; BRONSTED ACID; H BONDS; ETHERS; HYDROAMINATION; REARRANGEMENT; ALLENEDIENES; HETEROCYCLES; CARBOCYCLES; ALKYNES;

D O I：

10.1016/j.jorganchem.2015.05.034

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

An intermediate of the anellation reaction of phenols and 1,3-dienes could be detected, isolated and characterized as the hydroarylation product. The other conceivable intermediate, the hydroaryloxylation product, was prepared via Pd-catalysis and converted under the conditions of the gold catalysis, too. Under exactly the same conditions a very fast Claisen rearrangement took place delivering the formal hydroarylation product as well. After this fast intermolecular formation of the intermediate (formed either directly via the hydroarylation pathway or via a hydroaryloxylation/Claisen rearrangement sequence) the subsequent intramolecular reaction leading to the product turned out to be significantly slower. The major product is the cis-diastereomer (cis-3/trans-3 = 12:1). (C) 2015 Elsevier B.V. All rights reserved.

引用

页码：58 / 62

页数：5

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