Palladium-Catalyzed Intermolecular Aminoacetoxylation of Alkenes and the Influence of Phl(OAc)2 on Aminopalladation Stereoselectivity

被引：62
|
作者：
Martinez, Claudio [1 ]
Wu, Yichen [2 ]
Weinstein, Adam B. [3 ]
Stahl, Shannon S. [3 ]
Liu, Guosheng [2 ]
Muniz, Kilian [1 ,4 ]
机构：
[1] Inst Chem Res Catalonia ICIQ, Tarragona 43007, Spain
[2] Chinese Acad Sci, Shanghai Inst Organ Chem, Shanghai 200032, Peoples R China
[3] Univ Wisconsin, Dept Chem, Madison, WI 53706 USA
[4] Catalan Inst Res & Adv Studies ICREA, Barcelona 08010, Spain
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2013年 / 78卷 / 12期
基金：
美国国家科学基金会; 中国国家自然科学基金;
关键词：
N BOND FORMATION; REDUCTIVE ELIMINATION; C-O; CIS-AMINOPALLADATION; OXIDATIVE AMINATION; CARBON; REACTIVITY; COMPLEXES; MECHANISM; OLEFIN;
D O I：
10.1021/jo400671q
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A modified protocol has been identified for Pd-catalyzed intermolecular aininoacetoxylation of terminal and internal alkenes that enables the alkene to be used as the limiting reagent. The results prompt a reassessment of the stereochemical course of these reactions. X-ray crystallographic Characterization of two of the products, together with isotopic labeling studies, show that the amidopalladation step switches from a cis-selective process under aerobic conditions to a trans-selective process in the presence of diacetoxyiodobenzene.
引用
收藏
页码：6309 / 6315
页数：7
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