Regiospecific reductive elimination from diaryliodonium salts

Bijia Wang; Joseph W. Graskemper; Linlin Qin; Stephen G. DiMagno

doi:10.1002/anie.201000695

Regiospecific reductive elimination from diaryliodonium salts

Bijia Wang, Joseph W. Graskemper, Linlin Qin, Stephen G. DiMagno

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

86 Scopus citations

Abstract

(Figure Presented) Out-of-plane steric bulk furnished by a cyclophane substituent on iodine(III) strongly destabilizes the transition state in the reductive elimination from diaryliodonium salts and leads to regiochemical control (dubbed SECURE), as is demonstrated by computational and experimental studies. This approach should be general for high-valent maingroup and transition metal ions. X=N₃, OAc, PhO, CF₃CH₂O, SCN, PhS.

Original language	English (US)
Pages (from-to)	4079-4083
Number of pages	5
Journal	Angewandte Chemie - International Edition
Volume	49
Issue number	24
DOIs	https://doi.org/10.1002/anie.201000695
State	Published - Jun 1 2010
Externally published	Yes

Keywords

Cyclophanes
Iodanes
Reductive elimination
Regiochemistry
Stereoelectronic effects

ASJC Scopus subject areas

Catalysis
General Chemistry

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10.1002/anie.201000695

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title = "Regiospecific reductive elimination from diaryliodonium salts",

abstract = "(Figure Presented) Out-of-plane steric bulk furnished by a cyclophane substituent on iodine(III) strongly destabilizes the transition state in the reductive elimination from diaryliodonium salts and leads to regiochemical control (dubbed SECURE), as is demonstrated by computational and experimental studies. This approach should be general for high-valent maingroup and transition metal ions. X=N3, OAc, PhO, CF3CH2O, SCN, PhS.",

keywords = "Cyclophanes, Iodanes, Reductive elimination, Regiochemistry, Stereoelectronic effects",

author = "Bijia Wang and Graskemper, {Joseph W.} and Linlin Qin and DiMagno, {Stephen G.}",

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T1 - Regiospecific reductive elimination from diaryliodonium salts

AU - Wang, Bijia

AU - Graskemper, Joseph W.

AU - Qin, Linlin

AU - DiMagno, Stephen G.

PY - 2010/6/1

Y1 - 2010/6/1

N2 - (Figure Presented) Out-of-plane steric bulk furnished by a cyclophane substituent on iodine(III) strongly destabilizes the transition state in the reductive elimination from diaryliodonium salts and leads to regiochemical control (dubbed SECURE), as is demonstrated by computational and experimental studies. This approach should be general for high-valent maingroup and transition metal ions. X=N3, OAc, PhO, CF3CH2O, SCN, PhS.

AB - (Figure Presented) Out-of-plane steric bulk furnished by a cyclophane substituent on iodine(III) strongly destabilizes the transition state in the reductive elimination from diaryliodonium salts and leads to regiochemical control (dubbed SECURE), as is demonstrated by computational and experimental studies. This approach should be general for high-valent maingroup and transition metal ions. X=N3, OAc, PhO, CF3CH2O, SCN, PhS.

KW - Cyclophanes

KW - Iodanes

KW - Reductive elimination

KW - Regiochemistry

KW - Stereoelectronic effects

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JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 24

ER -

Regiospecific reductive elimination from diaryliodonium salts

Abstract

Keywords

ASJC Scopus subject areas

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