Rieke® Highly Reactive Zinc
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.
"Organozinc reagents prepared from highly reactive zinc." S. Kim and R.D. Rieke, Electronic Encyclopedia of Reagents for Organic Synthesis, (2012).
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.
"Negishi Cross-Coupling is Compatible with a Reactive B-CL Bond: Development of a Versatile Late-Stage Funtionalization of 1,2-Azaborines and It's Application to the Synthesis of New BN Isoteres of Naphthalene and Indeyl." Brown, Li and Liu, J. Am Chem Soc, 137 (2015) 8932.
Rieke, R.D and Seung-Hoi Kim, Organozinc Reagents Prepared From Highly Active Zinc, Encyclopedia of Reagents for Organic Synthesis [Online], John Wiley & Sons Ltd., http://onlinelibrary.wiley.com/book/10.1002/047084289X, DOI: 10.1002/047084289X.rn01505, Article Online Posting Date: September 14, 2012.
"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.
"A facile synthetic approach to the preparation of 3-pyridyl derivatives: preparations and coupling reactions of 3-pyridylzinc and Its analogues." S. Kim, T. Slocum and R.D.Rieke, SYNTHESIS, 22 (2009) 3823.
"A facile synthetic route for the preparation of 4-substituted 6-methyl-2-pyrone derivatives via organozinc reagents." S. Kim and R.D.Rieke, SYNLETT, 19 (2011) 2867.
Alternative Solvents for Organometallic reactions
"Solvent applications of 2-methyltetrahydrofuran in organometallic and biphasic reactions." David Aycock, Organic Process Research & Development, 11 (2007) 156-159.
"Alternative solvents: shades of green." J. Clark and S. Tavener, Organic Process Research & Development, 11 (2007) 149-155.
"Comparative performance evaluation and systematic screening of solvents in a range of Grignard reactions." A. Kadam et al., Green Chem, 15 (2013) 1880-1888.
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.
For applications see:
Organic Photovoltaic Cell (OPV)
- G. Li, V. Shrotriya, J. Huang, Y. Yao, T. Moriarty, K. Emery, Y. Yang, Nat. Mater. 2005, 4, 864.
- C. H. Woo, B. C. Thompson, B. J. Kim, M. F. Toney, J. M. J. Fréchet, J. Am. Chem. Soc. 2008, 130, 16324.
- T. Yamanari, T. Taima, K. Hara, K. Saito, J. Photochem. Photobiol. A 2006, 182, 269.
Organic Field-effect Transistor (OFET)
- Z. Bao, A. Dodabalapur, A. J. Lovinger, Appl. Phys. Lett. 1996, 69, 4108.
- L.-L. Chua, J. Zaumseil, J.-F. Chang, E. C.-W. Ou, P. K.-H. Ho, H. Sirringhaus, R. H. Friend, Nature 2005, 434, 194.
Organic Light-Emitting Diode (OLED)
- A. Dodabalapur, Z. Bao, A. Makhija, J. G. Laquindanum, V. R. Raju, Y. Feng, H. E. Katz, J. Rogers, Appl. Phys. Lett. 1998, 73, 142.
- S . D. D. V. Rughooputh, S. Hotta, A. J. Heeger, F. Wudl, J Polym. Sci. Part B: Plym. Phys. 1987, 25, 1071.
- A. Aoki, Hyomen Gijutsu (J. Surf. Finish. Soc. Jpn.) 2007, 58, 762.Photo-thermal-electrical Converter
- E. Miyako, C. Hosokawa, M. Kojima, M. Yudasaka, R. Funahashi, I. Oishi, Y. Hagihara, M. Shichiri, M. Takashima, K. Nishio, Y. Yoshida, Angew. Chem. Int. Ed. 2011, 50, 12266.
Flexible Fiber-type Transistor
- "Highly Conductive Graphene/Ag Hybrid Fibers for Flexible Fiber-Type Transistors." Sang, S.Y. et al, Nature Scientific Reports 5, Article number: 16366, 2015.