A New Route to Polykis(dialkylamino)benzenes and -naphthalenes Based on Protodefluorination of Electron-Rich Fluoroaromatics: Anion Radicals of Arenes as a Simple and Effective Alternative to ‘Classical’ LAH-Based Systems

Vladimir Igorevich Sorokin; Valery Anatolievich Ozeryanskii; Gennady Sergeevich Borodkin

doi:10.1055/s-2005-921755

PAPER

A New Route to Polykis(dialkylamino)benzenes and -naphthalenes Based on Protodefluorination of Electron-Rich Fluoroaromatics: Anion Radicals of Arenes as a Simple and Effective Alternative to ‘Classical’ LAH-Based Systems

Vladimir Igorevich Sorokin*^a, Valery Anatolievich Ozeryanskii^a, Gennady Sergeevich Borodkin^b
^a Department of Organic Chemistry, Rostov State University, Zorge street 7, 344090 Rostov-on-Don, Russia
Fax: +7(863)2974156; e-Mail: vsorokin@aaanet.ru;
^b Institute of Physical and Organic Chemistry, Stachki ave. 194/2, 344090 Rostov-on-Don, Russia

Abstract

All articles of this category

Abstract

A simple and effective procedure for protodefluorination of electron-rich fluoroaromatic compounds has been developed. It operates with aromatic anion radicals as reducing agents and shows superior results over ‘classical’ lithium aluminum hydride based systems.

Key words

fluorinated amino arenes - aromatic anion radicals - protodefluorination - lithium aluminum hydride - electron transfer

Full Text

References

<A NAME="RZ11505SS-1">1</A> Smith MB. March J. March’s Advanced Organic Chemistry John Wiley & Sons; New York: 2001. p.22-24

<A NAME="RZ11505SS-2">2</A> Krespan CG. In Chemistry of Organic Fluorine Compounds II: A Critical Review Hudlicky M. Pavlath AE. American Chemical Society; Washington: 1995. p.297-300

<A NAME="RZ11505SS-3">3</A> Kuhl S. Schneider R. Fort Y. Adv. Synth. Catal. 2003, 345: 341

<A NAME="RZ11505SS-4">4</A> Sorokin VI. Ozeryanskii VA. Borodkin GS. J. Fluorine Chem. 2005, in press

<A NAME="RZ11505SS-5">5</A> Sorokin VI. Ozeryanskii VA. Pozharskii AF. Eur. J. Org. Chem. 2004, 766

<A NAME="RZ11505SS-6A">6a</A> Goodson FE. Hauck SI. Hartwig JF. J. Am. Chem. Soc. 1999, 121: 7527

<A NAME="RZ11505SS-6B">6b</A> Ito A. Ono Y. Tanaka K. J. Org. Chem. 1999, 64: 8236

<A NAME="RZ11505SS-7">7</A> Aleksandrovskii YA. Bezhikina LV. Rodionov YV. Biokhimia (Moscow) 1981, 46: 708

<A NAME="RZ11505SS-8">8</A> Christensen JB. Schiødt N.-C. Bechgaard K. Buch-Rasmussen T. Acta Chem. Scand. 1996, 50: 1013

<A NAME="RZ11505SS-9A">9a</A> Hartwig JF. Angew. Chem. Int. Ed. 1998, 37: 2046

<A NAME="RZ11505SS-9B">9b</A> Prim D. Campagne J.-M. Joseph D. Andrioletti B. Tetrahedron 2002, 58: 2041

<A NAME="RZ11505SS-10">10</A> Seyden-Penne J. Reduction by the Alumino- and Borohydrides in Organic Synthesis Wiley-VCH; New York: 1997. p.224

<A NAME="RZ11505SS-11">11</A> Staab HA. Elbl-Weiser K. Krieger C. Eur. J. Org. Chem. 2000, 327

Stewart, J. J. P. MOPAC 6.0 Quantum Chemistry Program Exchange, University of Indiana, Bloomington, Indiana, USA.

<A NAME="RZ11505SS-13">13</A> Imamoto T. Takeyama T. Kusumoto T. Chem. Lett. 1985, 1491

<A NAME="RZ11505SS-14">14</A> Fuchibe K. Akiyama T. Synlett 2004, 1282

<A NAME="RZ11505SS-15">15</A> Everett S. In Chemistry of Organic Fluorine Compounds II: A Critical Review Hudlicky M. Pavlath AE. American Chemical Society; Washington: 1995. p.1037-1086

<A NAME="RZ11505SS-16">16</A> Wang HC. Levin G. Szwarc M. J. Am. Chem. Soc. 1978, 100: 3969

<A NAME="RZ11505SS-17">17</A> Rembaum A. Eisenberg A. Haack R. Landel RF. J. Am. Chem. Soc. 1967, 89: 1062

<A NAME="RZ11505SS-18">18</A> Arnett EM. Ko HC. Chao CC. J. Am. Chem. Soc. 1972, 94: 4776

<A NAME="RZ11505SS-19">19</A> Beletskaya IP. Bessmertnykh AG. Guilard R. Tetrahedron Lett. 1999, 40: 6393

<A NAME="RZ11505SS-20">20</A> Takeda N. Imamoto T. Org. Synth. 1998, 76: 228

<A NAME="RZ11505SS-21">21</A> Schröder U. Wadhawan J. Evans RG. Compton RG. Wood B. Walton DJ. France RR. Marken F. Page PCB. Hayman CM. J. Phys. Chem. B 2002, 106: 8697