Cationic Gold Catalyzes ω-Bromination of Terminal Alkynes and Subsequent Hydroaddition Reactions

被引：33

作者：

Leyva-Perez, Antonio ^{[1
]}

Rubio-Marques, Paula ^{[1
]}

Al-Deyab, Salem S. ^{[2
]}

Al-Resayes, Saud I. ^{[2
]}

Corma, Avelino ^{[1
,2
]}

机构：

[1] Univ Politecn Valencia, Inst Tecnol Quim, Consejo Super Invest Cient, Valencia 46022, Spain

[2] King Saud Univ, Coll Sci, Dept Chem, Riyadh 11451, Saudi Arabia

来源：

ACS CATALYSIS | 2011年 / 1卷 / 06期

关键词：

gold catalysis; aurophilic interactions; terminal alkynes; sigma; pi-bisfunctionalization; bromoalkynes; BOND-FORMING REACTIONS; ONE-POT SYNTHESIS; INTERMOLECULAR HYDROAMINATION; ORGANOGOLD COMPOUNDS; ROOM-TEMPERATURE; LEWIS-ACID; COMPLEXES; ACTIVATION; ACETYLIDES; EFFICIENT;

D O I：

10.1021/cs200168p

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

Orthogonal sigma,pi-bisfunctionalization of terminal alkynes can be achieved with a cationic gold complex in catalytic amounts. First, the terminal C-H bond is transformed to the corresponding bromoalkyne which is then activated toward nucleophilic attack. This reactivity correlates with the structural nature of isolated gold-alkyne complexes.

引用

页码：601 / 606

页数：6

共 70 条

[51] Concise synthesis of the CDE ring system of tetrahydroisoquinoline alkaloids using carbophilic Lewis acid-catalyzed hydroamidation and oxidative Friedel-Crafts cyclization
Obika, Shingo
Yasui, Yoshizumi
Yanada, Reiko
Takemoto, Yoshiji
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (13) : 5206 - 5209
[52] AZABENZOCYCLOHEPTENONES .6. PREPARATION AND SOME REACTIONS OF I,2,4,5-TETRAHYDRO-I-OXO-3-TOLUENE-P-SULPHONYLBENZ[D]AZEPINE
REHMAN, MA
PROCTOR, GR
[J]. JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1967, (01): : 58 - &
[53] Integrating carbon-halogen bond formation into medicinal plant metabolism
Runguphan, Weerawat
Qu, Xudong
O'Connor, Sarah E.
[J]. NATURE, 2010, 468 (7322) : 461 - U294
[54] Regioselective transformation of alkynes into cyclic acetals and thioacetals with a gold(I) catalyst: comparison with Bronsted acid catalysts
Santos, Laura L.
Ruiz, Violeta R.
Sabater, Maria J.
Corma, Avelino
[J]. TETRAHEDRON, 2008, 64 (34) : 7902 - 7909
[55] Gold η2-Coordination to Unsaturated and Aromatic Hydrocarbons: The Key Step in Gold-Catalyzed Organic Transformations
Schmidbaur, Hubert
Schier, Annette
[J]. ORGANOMETALLICS, 2010, 29 (01) : 2 - 23
[56] Unusual Carbon-Carbon Bond Formations between Allylboronates and Acetals or Ketals Catalyzed by a Peculiar Indium(I) Lewis Acid
Schneider, Uwe
Dao, Hai T.
Kobayashi, Shu
[J]. ORGANIC LETTERS, 2010, 12 (11) : 2488 - 2491
[57] Mechanism of Reductive Elimination of Methyl Iodide from a Novel Gold(III)-Monomethyl Complex
Scott, Valerie J.
Labinger, Jay A.
Bercaw, John E.
[J]. ORGANOMETALLICS, 2010, 29 (18) : 4090 - 4096
[58] Elementary Steps in Gold Catalysis: The Significance of gem-Diauration
Seidel, Guenter
Lehmann, Christian W.
Fuerstner, Alois
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (45) : 8466 - 8470
[59] Gold(I)-Catalyzed Enantioselective Polycyclization Reactions
Sethofer, Steven G.
Mayer, Timo
Toste, F. Dean
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (24) : 8276 - +
[60] Gold (I)-catalyzed 5-endo-dig carbocyclization of acetylenic dicarbonyl compounds
Staben, ST
Kennedy-Smith, JJ
Toste, FD
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (40) : 5350 - 5352

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