Palladium-Catalyzed, Chelation-Assisted Stereo- and Regioselective Synthesis of Tetrasubstituted Olefins by Oxidative Heck Arylation

被引：45

作者：

Lee, Hyun Seung ^{[1
,2
]}

Kim, Ko Hoon ^{[1
,2
]}

Kim, Sung Hwan ^{[1
,2
]}

Kim, Jae Nyoung ^{[1
,2
]}

机构：

[1] Chonnam Natl Univ, Dept Chem, Kwangju 500757, South Korea

[2] Chonnam Natl Univ, Inst Basic Sci, Kwangju 500757, South Korea

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2012年 / 354卷 / 13期

基金：

新加坡国家研究基金会;

关键词：

chelation; Morita-Baylis-Hillman adducts; oxidative Heck arylation; palladium; BAYLIS-HILLMAN REACTION; HIGHLY SELECTIVE ARYLATION; ELECTRON-DEFICIENT ARENES; C-H FUNCTIONALIZATION; ARYLBORONIC ACIDS; STEREOSELECTIVE-SYNTHESIS; METALATION-DEPROTONATION; COUPLING REACTION; INTERNAL ALKYNES; ALLYLIC ESTERS;

D O I：

10.1002/adsc.201200306

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

An efficient synthesis of tetrasubstituted olefins was achieved via a palladium-catalyzed, chelation-assisted oxidative Heck arylation protocol from trisubstituted olefins bearing a tether with a directing group in a completely stereo- and regioselective manner. The stereo- and regioselectivity as well as excellent yields of tetrasubstituted olefins originated from the stabilization of a palladium intermediate by chelation between the palladium center and a directing group.

引用

页码：2419 / 2426

页数：8

共 101 条

[1]

[Anonymous], ANGEW CHEM

[2]

[Anonymous], 2012, ANGEW CHEM-GER EDIT

[3]

[Anonymous], 2001, Angew. Chem., Int. Ed, DOI [DOI 10.1002/1521-3757(20010401)113:7ANDLT

[4]

1331::AID-ANGE1331ANDGT

[5]

3.0.CO

[6]

2-S, 10.1002/1521-3757(20010401)113:7andlt

[7]

1331::AID-ANGE1331andgt

[8]

3.0.CO

[9]

2-S]

[10] Palladium-Catalyzed Direct Arylation of Heteroaromatic Compounds: Improved Conditions Utilizing Controlled Microwave Heating [J].

Baghbanzadeh, Mostafa ;

Pilger, Christian ;

Kappe, C. Oliver .

JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (19) :8138-8142

← 1 2 3 4 5 6 7 8 9 10 →