Tetrahedron letters

Copper catalyzed magnesium-Barbier reaction for γ-selective alkyl–allyl coupling

E Erdik, M Koçoğlu

Index: Erdik, Ender; Kocoglu, Melike Tetrahedron Letters, 2007 , vol. 48, # 24 p. 4211 - 4214

Full Text: HTML

Citation Number: 9

Abstract

CuCN catalyzed alkyl–allyl coupling under magnesium-Barbier conditions occurs regioselectively and affords predominantly the γ-products in good to high yields. This one- pot CuCN catalyzed reaction utilising Mg, an alkyl halide and an allylic substrate in THF at room temperature provides an easy alternative to the classical CuCN catalyzed γ-allylation of alkyl Grignard reagents.

Related Articles:

A convenient coupling reaction of allyl alcohols with grignard reagents using 1-chloro-2-methyl-N, N-tetramethylenepropenylamine

[Fujisawa, Tamotsu; Iida, Sachio; Yukizaki, Hisashi; Sato, Toshio Tetrahedron Letters, 1983 , vol. 24, # 51 p. 5745 - 5748]

A Telluride-Triggered Nucleophilic Ring Opening of Monoactivated Cyclopropanes1

[Charette, Andre B.; Naud, Julie Tetrahedron Letters, 1998 , vol. 39, # 40 p. 7259 - 7262]

An Alkyl??Aluminium Promoted Stereospecific Addition to Vinyl Olefins

[Stefani,A. Helvetica Chimica Acta, 1973 , vol. 56, # 4 p. 1192 - 1198]

Coupling reactions of higher order cuprates with primary halides: extremely mild and efficient substitution reactions of bromides and chlorides

[Lipshutz, Bruce H.; Parker, David; Kozlowski, Joseph A.; Miller, Robert D. Journal of Organic Chemistry, 1983 , vol. 48, # 19 p. 3334 - 3336]

Coupling reactions of higher order cuprates with primary halides: extremely mild and efficient substitution reactions of bromides and chlorides

[Lipshutz, Bruce H.; Parker, David; Kozlowski, Joseph A.; Miller, Robert D. Journal of Organic Chemistry, 1983 , vol. 48, # 19 p. 3334 - 3336]

More Articles...