Nucleophile-Selective Cross-Coupling Reactions with Vinyl and Alkynyl Bromides on a Dinucleophilic Aromatic Substrate

被引：11

作者：

He, Lu-Ying ^{[1
]}

Schulz-Senft, Mathias ^{[1
]}

Thiedemann, Birk ^{[1
]}

Linshoeft, Julian ^{[1
]}

Gates, Paul J. ^{[2
]}

Staubitz, Anne ^{[1
]}

机构：

[1] Univ Kiel, Otto Diels Inst Organ Chem, D-24098 Kiel, Germany

[2] Univ Bristol, Sch Chem, Bristol BS8 1TS, Avon, England

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2015年 / 2015卷 / 11期

基金：

英国工程与自然科学研究理事会;

关键词：

Cross-coupling; Palladium; C-C coupling; Chemoselectivity; Sulfur heterocycles; ALPHA; BETA-UNSATURATED CARBOXYLIC-ACIDS; EFFICIENT SYNTHESIS; BORYLATION; REAGENTS; HALIDES;

D O I：

10.1002/ejoc.201500138

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A nucleophile-selective cross-coupling reaction on an aromatic compound bearing two metal groups, Bpin and SnMe3, has been developed. Previously, only aryl bromides and iodides could be used as electrophilic components, but in this work, the scope could be extended to vinyl and alkynyl bromides as electrophiles. This means that the roles typical in Sonogashira couplings or Heck reactions of the aromatic ring as the dielectrophile coupling to vinyl and alkynyl metal species are reversed, which presents a new tool for organic synthesis. The first nucleophilic site to react is the stannyl group, and subsequently, a Suzuki-Miyaura cross-coupling reaction can take place on the same molecule.

引用

页码：2498 / 2502

页数：5

共 51 条

[1] Mechanism of the palladium-catalyzed homocoupling of arylboronic acids: Key involvement of a palladium peroxo complex
Adamo, Carlo
Amatore, Christian
Ciofini, Ilaria
Jutand, Anny
Lakmini, Hakim
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (21) : 6829 - 6836
[2] Theoretical evidence for low-ligated palladium(0): [Pd-L] as the active species in oxidative addition reactions
Ahlquist, M
Fristrup, P
Tanner, D
Norrby, PO
[J]. ORGANOMETALLICS, 2006, 25 (08) : 2066 - 2073
[3] Efficient synthesis of diverse hetero-bis-metallated alkenes as modular reagents towards highly conjugated and isolated olefinic systems
Altendorfer, Mario
Menche, Dirk
[J]. CHEMICAL COMMUNICATIONS, 2012, 48 (66) : 8267 - 8269
[4] Copper-mediated cross-coupling reactions of N-unsubstituted sulfoximines and aryl halides
Cho, GY
Rémy, P
Jansson, J
Moessner, C
Bolm, C
[J]. ORGANIC LETTERS, 2004, 6 (19) : 3293 - 3296
[5] Total synthesis of 2′-O-methylmyxalamide D and (6E)-2′-O-methylmyxalamide D
Coleman, Robert S.
Lu, Xiaoling
Modolo, Isabelle
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (13) : 3826 - +
[6] Tandem Stille/Suzuki-Miyaura coupling of a hetero-bis-metalated diene. Rapid, one-pot assembly of polyene systems
Coleman, RS
Walczak, MC
[J]. ORGANIC LETTERS, 2005, 7 (11) : 2289 - 2291
[7] Crawley M. L., 2012, Applications of Transition Metal Catalysis in Drug Discovery and Development: An Industrial Perspective
[8] Catalytic hunsdiecker reaction of α,β-unsaturated carboxylic acids:: How efficient is the catalyst?
Das, JP
Roy, S
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (22) : 7861 - 7864
[9] Fujii S., 2011, Angew. Chem., V123, P8008
[10] Total Synthesis of Synechoxanthin through Iterative Cross-Coupling
Fujii, Seiko
Chang, Stephanie Y.
Burke, Martin D.
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (34) : 7862 - 7864

← 1 2 3 4 5 6 →