Generation of aryl anions by double electron transfer to aryl iodides from a neutral ground-state organic super electron donor (SED)

J.A. Murphy, S. Zhou, C.T. Tuttle, F. Schoenebeck, M. Mohan, S.R. Park, L.E.A. Berlouis, D.W. Thomson

Research output: Contribution to journalArticle

87 Citations (Scopus)

Abstract

Stabilized carbanions can be prepared by deprotonation of the corresponding carbon acids, but more reactive carbanions, such as aryl anions, are usually made
by metal–halogen exchange or by electrochemical routes.[1] Whereas the use of metals and organometallic compounds to form aryl anions is well established, the
use of totally organic electron-transfer agents, in the absence of photochemical
activation, is completely unknown.[2] Herein we report the first neutral organic
molecule to achieve this feat.
Original languageEnglish
Pages (from-to)5178-5183
Number of pages6
JournalAgewandte Chemie-International Edition
Volume46
DOIs
Publication statusPublished - 2007

Fingerprint

Iodides
Ground state
Anions
Negative ions
Organometallic Compounds
Deprotonation
Electrons
Organometallics
Ion exchange
Carbon
Metals
Acids

Keywords

  • aryl anions
  • synthetic methods
  • reduction
  • electron transfer

Cite this

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Generation of aryl anions by double electron transfer to aryl iodides from a neutral ground-state organic super electron donor (SED). / Murphy, J.A.; Zhou, S.; Tuttle, C.T.; Schoenebeck, F.; Mohan, M.; Park, S.R.; Berlouis, L.E.A.; Thomson, D.W.

In: Agewandte Chemie-International Edition, Vol. 46, 2007, p. 5178-5183.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Generation of aryl anions by double electron transfer to aryl iodides from a neutral ground-state organic super electron donor (SED)

AU - Murphy, J.A.

AU - Zhou, S.

AU - Tuttle, C.T.

AU - Schoenebeck, F.

AU - Mohan, M.

AU - Park, S.R.

AU - Berlouis, L.E.A.

AU - Thomson, D.W.

PY - 2007

Y1 - 2007

N2 - Stabilized carbanions can be prepared by deprotonation of the corresponding carbon acids, but more reactive carbanions, such as aryl anions, are usually made by metal–halogen exchange or by electrochemical routes.[1] Whereas the use of metals and organometallic compounds to form aryl anions is well established, the use of totally organic electron-transfer agents, in the absence of photochemical activation, is completely unknown.[2] Herein we report the first neutral organic molecule to achieve this feat.

AB - Stabilized carbanions can be prepared by deprotonation of the corresponding carbon acids, but more reactive carbanions, such as aryl anions, are usually made by metal–halogen exchange or by electrochemical routes.[1] Whereas the use of metals and organometallic compounds to form aryl anions is well established, the use of totally organic electron-transfer agents, in the absence of photochemical activation, is completely unknown.[2] Herein we report the first neutral organic molecule to achieve this feat.

KW - aryl anions

KW - synthetic methods

KW - reduction

KW - electron transfer

UR - http://dx.doi.org/10.1002/anie.200700554

U2 - 10.1002/anie.200700554

DO - 10.1002/anie.200700554

M3 - Article

VL - 46

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EP - 5183

JO - Angewandte Chemie International Edition

JF - Angewandte Chemie International Edition

SN - 1433-7851

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