Literature
No need for a drybox or a solvent still. Simply cannulate Rieke® Metals in THF into a reaction flask under an atmosphere of argon or nitrogen.
Rieke® Highly Reactive Zinc
The use of CuI is patented by Rieke Metals, Inc.
For a full paper on the direct formation of fuctionalized Organozinc reagents and their reactions with acid chlorides, alpha,beta-unsaturated ketones and allylic, aryl, and vinyl halides, see: L. Zhu, R. Wehmeyer and R. Rieke. Journal of Organic Chemistry, 56 (1991) 1445.
For experimental details see: Reuben D. Rieke and Mark V. Hanson, Chapter 2, "Practical Approach in Organozinc Reagents" Edited by Paul Knochel and Philip Jones (Oxford University Press).
For detailed mechanistic studies and relative rates of reactions, see: A. Guijarro, D.M. Rosenberg and R.D. Rieke, J. of the American Chemical Society 121 (1999) 4155.
For a review of Rieke® Highly Reactive Zinc chemistry, see: Reuben D. Rieke and Mark V. Hanson, Tetrahedron, 53 (1997) 1925 and leading references.
Rieke® Magnesium
For a review of Rieke® Magnesium chemistry, see: Reuben D. Rieke and Mark V. Hanson, Tetrahedron, 53 (1997) 1925 and leading references.
For more details and references see: R.D. Rieke, et al, Chapter 4, Handbook of Grignard Reagents Edited by Gary S. Silverman and Philip E. Rakita, Marcel Dekker, Inc. 1996.
Rieke® Semi-Conducting Polymers
For physical properties and additional references for our regioregular and regiorandom 3-alkyl polythiophenes see:
T. Chen and R.D. Rieke, J. Am. Chem. Soc. 114 (1992) 10087.
T. Chen and R.D. Rieke, Synth. Mat, 60 (1993) 175.
T. Chen, X. Wu, and R.D. Rieke, J. Am. Chem. Soc. 117 (1995) 233.
Organozinc Chemistry
"Coupling reactions with haloaromatic amines and alcohols for a practical synthetic route to 2-substituted aminophenyl and hydroxyphenyl pyridines." S. Kim and R.D. Rieke, Tetrahedron Letters, 50 (2009) 6985.
"A convenient synthesis of 5-aryl- and 5-heteroaryl-2-furaldehydes by the cross-coupling reaction of ogranozincs." S. Kim and R.D. Rieke, Tetrahedron Letters, 51 (2010) 2657.
"5-Bromo-2-pyridylzinc reagent; direct preparation and its coupling reactions." R.D. Rieke and S. Kim, Tetrahedron Letters, 52 (2011) 244.
"A novel organozinc reagent 4-coumarinylzinc bromide; preparation and application in the synthesis of 4-substituted coumarin derivatives." R.D. Rieke and S. Kim, Tetrahedron Letters, 52 (2011) 3094.
"A facile synthetic route for 2-pyridyl derivatives: direct preparation of a stable 2-pyridylzinc bromide and its copper-free and Pd-catalyzed coupling reactions." S. Kim, T. Slocum and R.D. Rieke, Tetrahedron Letters, 50 (2009) 5329.
"5-(1,3-Dioxolan-2-yl)-2-furanylzinc bromide; direct preparation and its application for the synthesis of 5-substituted furan derivatives." R.D. Rieke and S. Kim, Tetrahedron Letters, 52 (2011) 1128.
"Preparation of aryl ketones via Ni-catalyzed Negishi-coupling reactions with acid chlorides." S. Kim and R.D. Rieke, Tetrahedron Letters, 52 (2011) 1523. |