Unexpected tandem Sonogashira-carbopalladation-Sonogashira coupling reaction of benzyl halides with terminal alkynes: A novel four-component domino sequence to highly substituted enynes

被引：22

作者：

Pottier, LR ^{[1
]}

Peyrat, JF ^{[1
]}

Alami, M ^{[1
]}

Brion, JD ^{[1
]}

机构：

[1] Univ Paris 11, Fac Pharm, CNRS, UMR 8076,BioCIS,Lab Chim Therapeut, F-92296 Chatenay Malabry, France

来源：

SYNLETT | 2004年 / 09期

关键词：

Sonogashira; palladium; enynes; benzyl halides; alkynes; four-component coupling;

D O I：

10.1055/s-2004-829079

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Unexpected reactivity of benzyl halides with 1-alkynes in Sonogashira reaction promotes in a single-step process the construction of three carbon-carbon bonds regio- and stereoselectively and afforded highly substituted enynes in fair to good yields. The formation of the coupling adduct in this palladium-mediated four-component domino procedure is rationalized by an unprecedented tandem Sonogashira benzylpalladation Sonogashira sequence.

引用

页码：1503 / 1508

页数：6

共 3 条

[1] Transition metal control in the reaction of alkyne-substituted phenyl iodides with terminal alkynes:: Sonogashira coupling vs cyclic carbopalladation
Teply, F
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[J]. TETRAHEDRON, 2002, 58 (44) : 9007 - 9018
[2] A Novel Protocol for the Cu-Catalyzed Sonogashira Coupling Reaction between Aryl Halides and Terminal Alkynes using trans-1,2-Diaminocyclohexane Ligand
Asha, Sujatha
Thomas, Anns Maria
Ujwaldev, Sankuviruthiyil M.
Anilkumar, Gopinathan
[J]. CHEMISTRYSELECT, 2016, 1 (13): : 3938 - 3941
[3] Three-component tandem reaction involving acid chlorides, terminal alkynes, and ethyl 2-amino-1H-indole-3-carboxylates: synthesis of highly diversified pyrimido[1,2-a]indoles via sequential Sonogashira and [3+3] cyclocondensation reactions
Gupta, Sahaj
Sharma, Sudhir K.
Mandadapu, Anil K.
Gauniyal, Harsh M.
Kundu, Bijoy
[J]. TETRAHEDRON LETTERS, 2011, 52 (33) : 4288 - 4291

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