Tetrahedron Letters

An unprecedented iron-catalyzed cross-coupling of primary and secondary alkyl Grignard reagents with non-activated aryl chlorides

MC Perry, AN Gillett, TC Law

Index: Perry, Marc C.; Gillett, Amber N.; Law, Tyler C. Tetrahedron Letters, 2012 , vol. 53, # 33 p. 4436 - 4439

Full Text: HTML

Citation Number: 14

Abstract

The use of N-heterocyclic carbene ligands in the iron-catalyzed cross-coupling of alkyl Grignards has allowed, for the first time, coupling of non-activated, electron rich aryl chlorides. Surprisingly, the tetrahydrate of FeCl2 was found to be a better pre-catalyst than anhydrous FeCl2. Primary Grignard reagents coupled in excellent yields while secondary Grignard reagents coupled in modest yields. The use of acyclic secondary Grignard ...

Related Articles:

Palladium-catalyzed cross-coupling reactions of triorganoindium compounds with vinyl and aryl triflates or iodides

[Perez, Ignacio; Sestelo, Jose Perez; Sarandeses, Luis A. Organic Letters, 1999 , vol. 1, # 8 p. 1267 - 1269]

Atom-efficient metal-catalyzed cross-coupling reaction of indium organometallics with organic electrophiles

[Perez; Sestelo; Sarandeses Journal of the American Chemical Society, 2001 , vol. 123, # 18 p. 4155 - 4160]

Atom-efficient metal-catalyzed cross-coupling reaction of indium organometallics with organic electrophiles

[Perez; Sestelo; Sarandeses Journal of the American Chemical Society, 2001 , vol. 123, # 18 p. 4155 - 4160]

Microwave-assisted silica-supported aluminum chloride-catalyzed Friedel-Crafts alkylation

[Zupp, Laurine R.; Campanella, Veronica L.; Rudzinski, Diandra M.; Beland, Franois; Priefer, Ronny Tetrahedron Letters, 2012 , vol. 53, # 39 p. 5343 - 5346]

… leaving group at benzylic position: application to a three-component coupling of p-iodobenzyl derivatives, trialkylzincates, and electrophiles leading to functionalized p …

[Harada, Toshiro; Kaneko, Takayuki; Fujiwara, Takayuki; Oku, Akira Tetrahedron, 1998 , vol. 54, # 32 p. 9317 - 9332]

More Articles...