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:
For experimental details see:
For detailed mechanistic studies and relative rates of reactions, see:
For a review of Rieke® Highly Reactive Zinc chemistry, see:
“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.
“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.
For physical properties and additional references for our regioregular and regiorandom 3-alkyl polythiophenes see:
For applications see:
Organic Photovoltaic Cell (OPV)
Organic Field-effect Transistor (OFET)
Organic Light-Emitting Diode (OLED)
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.