Palladium-catalyzed oxyarylation of olefins using silver carbonate as the base. Probing the mechanism by electrospray ionization mass spectrometry

被引：22
作者：
Buarque, Camilla D. [2 ]
Pinho, Vagner D. [2 ]
Vaz, Boniek Gontijo [1 ]
Eberlin, Marcos N. [1 ]
da Silva, Alcides J. M. [2 ]
Costa, Paulo R. R. [2 ]
机构：
[1] Univ Estadual Campinas, Lab ThoMSon Espectrometria Massas, Inst Quim, BR-13083970 Sao Paulo, Brazil
[2] Univ Fed Rio de Janeiro, Lab Quim Bioorgan, Nucleo Pesquisa Produtos Nat, Ctr Ciencia Saude, BR-21941590 Rio De Janeiro, RJ, Brazil
来源：
JOURNAL OF ORGANOMETALLIC CHEMISTRY | 2010年 / 695卷 / 18期
基金：
巴西圣保罗研究基金会;
关键词：
Oxyarylation; ortho-Iodophenols; Pterocarpans; Palladium catalyst; Mass spectrometry; Oxa-Heck; PRELIMINARY PHARMACOLOGICAL EVALUATION; ANNULATED GAMMA-CARBOLINES; HECK REACTION; INTERNAL ALKYNES; ARYLATION; REGIOSELECTIVITY; HETEROANNULATION; OXYPHENYLATION; TELLURIDES; INDOLES;
D O I：
10.1016/j.jorganchem.2010.05.014
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
The Pd(OAc)(2)-catalyzed oxyarylation of electron-rich (8 and 12) and electron-poor (10) olefins by ortho-iodophenols (3a-d) was studied using Ag(2)CO(3) as the base, in acetone, and in the presence and absence of PPh(3). The corresponding adducts of oxyarylation were obtained in moderate yields. The reaction mechanism was examined by electrospray ionization mass spectrometry (ESI-MS). Cationic arylpalladium intermediate (14), formed by the oxidative insertion of Pd(0) into 3a, and the cationic palladacycles (15), obtained by reaction of 14 with olefins 8 and 12, were intercepted by ESI-MS and characterized by ESI-MS/MS. (c) 2010 Elsevier B.V. All rights reserved.
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收藏
页码：2062 / 2067
页数：6
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