A novel route to organonitrites by Pd-catalyzed crosscoupling of metal nitrite and potassium organotrifluoroborates

Nabil Saleh, Tennessee State University

Abstract

Aromatic nitration is a very important synthetic process in pharmaceuticals, dyes and other industries. Classical synthesis of these aromatic nitro compounds uses nitric acid as the nitrite source with sulfuric acid as catalyst. In new methodology, transition metal-catalyzed cross-coupling chemistry is being used to create these compounds in more efficient and environmentally friendly way. Buchwald and Saito have shown cross-coupling nitration reactions involving aryl halides to be possible. In our case, we explored the use of organotrifluoroborates, a very reactive boron species in cross-coupling chemistry. We discovered a new protocol for organonitrite by palladium-catalyzed cross-coupling of sodium nitrite and potassium organotrifluoroborates under microwave irradiation. This work demonstrates a new synthetic route to aromatic nitrites. We also attempted the same kind of coupling chemistry by using bismuth nitrate. This new transformation of organonitrite by cross-coupling chemistry has been successfully established.^

Subject Area

Chemistry, Organic

Recommended Citation

Nabil Saleh, "A novel route to organonitrites by Pd-catalyzed crosscoupling of metal nitrite and potassium organotrifluoroborates" (2013). ETD Collection for Tennessee State University. Paper AAI1547311.
http://digitalscholarship.tnstate.edu/dissertations/AAI1547311

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