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

收藏

页码：2419 / 2426

页数：8

相关论文

共 101 条

[41] Transition-Metal-Catalyzed Oxidative Heck Reactions [J].

Karimi, Babak ;

Behzadnia, Hesam ;

Elhamifar, Dawood ;

Akhavan, Pari Fadavi ;

Esfahani, Farhad Kabiri ;

Zamani, Asghar .

SYNTHESIS-STUTTGART, 2010, (09) :1399-1427

[42] Synthesis of cyclic compounds from the Baylis-Hillman adducts [J].

Kim, JN ;

Lee, KY .

CURRENT ORGANIC CHEMISTRY, 2002, 6 (07) :627-645

[43] Palladium-catalyzed oxidative arylation of chromones via a double C-H activation: an expedient approach to flavones [J].

Kim, Ko Hoon ;

Lee, Hyun Seung ;

Kim, Se Hee ;

Kim, Jae Nyoung .

TETRAHEDRON LETTERS, 2012, 53 (22) :2761-2764

[44] Palladium(II)-catalyzed oxidative homo-coupling of 1,3-dimethyluracil derivatives [J].

Kim, Ko Hoon ;

Lee, Hyun Seung ;

Kim, Sung Hwan ;

Kim, Jae Nyoung .

TETRAHEDRON LETTERS, 2012, 53 (11) :1323-1327

[45] Palladium-catalyzed direct 5-arylation of 1,3-dimethyluracil with aryl bromides: an electrophilic metalation-deprotonation with electrophilic arylpalladium intermediate [J].

Kim, Ko Hoon ;

Lee, Hyun Seung ;

Kim, Jae Nyoung .

TETRAHEDRON LETTERS, 2011, 52 (47) :6228-6233

[46] Palladium-catalyzed synthesis of indane and cyclobuta[a]indenes from homoallylic alcohols derived from Baylis-Hillman adducts: base-dependent stereoselectivity for the benzylidene group in cyclobuta[a]indene [J].

Kim, Ko Hoon ;

Kim, Se Hee ;

Park, Sunhong ;

Kim, Jae Nyoung .

TETRAHEDRON, 2011, 67 (19) :3328-3336

[47] Palladium- and nickel-catalyzed coupling reactions of α-bromoalkenylphosphonates with arylboronic acids and lithium alkenylborates [J].

Kobayashi, Y ;

William, AD .

ADVANCED SYNTHESIS & CATALYSIS, 2004, 346 (13-15) :1749-1757

[48] Tetraphosphine/palladium-catalyzed Heck reactions of aryl halides with disubstituted alkenes [J].

Kondolff, I ;

Doucet, H ;

Santelli, M .

TETRAHEDRON LETTERS, 2003, 44 (46) :8487-8491

[49] Palladium-catalyzed benzene arylation: Incorporation of catalytic pivalic acid as a proton shuttle and a key element in catalyst design [J].

Lafrance, Marc ;

Fagnou, Keith .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (51) :16496-16497

[50] Intermolecular Dehydrogenative Heck Reactions [J].

Le Bras, Jean ;

Muzart, Jacques .

CHEMICAL REVIEWS, 2011, 111 (03) :1170-1214

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