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

doi:10.1002/anie.200700554

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

Pure And Applied Chemistry

Research output: Contribution to journal › Article › peer-review

121 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 language	English
Pages (from-to)	5178-5183
Number of pages	6
Journal	Agewandte Chemie-International Edition
Volume	46
DOIs	https://doi.org/10.1002/anie.200700554
Publication status	Published - 2007

Keywords

aryl anions
synthetic methods
reduction
electron transfer

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10.1002/anie.200700554

Cite this

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

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.",

keywords = "aryl anions, synthetic methods, reduction, electron transfer",

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

year = "2007",

doi = "10.1002/anie.200700554",

language = "English",

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pages = "5178--5183",

journal = "Agewandte Chemie-International Edition",

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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

SN - 1433-7851

VL - 46

SP - 5178

EP - 5183

JO - Agewandte Chemie-International Edition

JF - Agewandte Chemie-International Edition

ER -

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

Abstract

Keywords

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Physical Organic Chemistry: Opportunities In Synthesis, Materials And Pharmaceuticals (Science And Innovation Award)

New horizons in organic electron transfer

Cite this

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

Abstract

Keywords

Access to Document

Other files and links

Fingerprint

Projects

Physical Organic Chemistry: Opportunities In Synthesis, Materials And Pharmaceuticals (Science And Innovation Award)

New horizons in organic electron transfer

Cite this