Mechanistic complexity in organo-SOMO activation

James J. Devery; Jay C. Conrad; David W.C. MacMillan; Robert A. Flowers

doi:10.1002/anie.201001673

Mechanistic complexity in organo-SOMO activation

James J. Devery, Jay C. Conrad, David W.C. MacMillan, Robert A. Flowers

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

72 Scopus citations

Abstract

Wet chemistry: Organo-SOMO activation is an intricate process. The catalyst is deactivated in the absence of H2O and its concentration is maintained with 2 equivalents of H2O. The kinetic role of ceric ammonium nitrate (CAN) is masked by phase transfer and its limited solubility is enhanced by added H2O. Mechanistic studies show that careful addition of H2O to dried reagents greatly enhances reaction. TMS=trimethylsilyl.

Original language	English (US)
Pages (from-to)	6106-6110
Number of pages	5
Journal	Angewandte Chemie - International Edition
Volume	49
Issue number	35
DOIs	https://doi.org/10.1002/anie.201001673
State	Published - Aug 16 2010

All Science Journal Classification (ASJC) codes

General Chemistry
Catalysis

Keywords

Ceric ammonium nitrate
Organocatalysis
Phase transfer
Reaction mechanisms
Single electron transfer

Access to Document

10.1002/anie.201001673

Cite this

@article{7d4ac91c648f4b879118c2dec009ffbb,

title = "Mechanistic complexity in organo-SOMO activation",

abstract = "Wet chemistry: Organo-SOMO activation is an intricate process. The catalyst is deactivated in the absence of H2O and its concentration is maintained with 2 equivalents of H2O. The kinetic role of ceric ammonium nitrate (CAN) is masked by phase transfer and its limited solubility is enhanced by added H2O. Mechanistic studies show that careful addition of H2O to dried reagents greatly enhances reaction. TMS=trimethylsilyl.",

keywords = "Ceric ammonium nitrate, Organocatalysis, Phase transfer, Reaction mechanisms, Single electron transfer",

author = "Devery, {James J.} and Conrad, {Jay C.} and MacMillan, {David W.C.} and Flowers, {Robert A.}",

year = "2010",

month = aug,

day = "16",

doi = "10.1002/anie.201001673",

language = "English (US)",

volume = "49",

pages = "6106--6110",

journal = "Angewandte Chemie - International Edition",

issn = "1433-7851",

publisher = "John Wiley and Sons Ltd",

number = "35",

}

TY - JOUR

T1 - Mechanistic complexity in organo-SOMO activation

AU - Devery, James J.

AU - Conrad, Jay C.

AU - MacMillan, David W.C.

AU - Flowers, Robert A.

PY - 2010/8/16

Y1 - 2010/8/16

N2 - Wet chemistry: Organo-SOMO activation is an intricate process. The catalyst is deactivated in the absence of H2O and its concentration is maintained with 2 equivalents of H2O. The kinetic role of ceric ammonium nitrate (CAN) is masked by phase transfer and its limited solubility is enhanced by added H2O. Mechanistic studies show that careful addition of H2O to dried reagents greatly enhances reaction. TMS=trimethylsilyl.

AB - Wet chemistry: Organo-SOMO activation is an intricate process. The catalyst is deactivated in the absence of H2O and its concentration is maintained with 2 equivalents of H2O. The kinetic role of ceric ammonium nitrate (CAN) is masked by phase transfer and its limited solubility is enhanced by added H2O. Mechanistic studies show that careful addition of H2O to dried reagents greatly enhances reaction. TMS=trimethylsilyl.

KW - Ceric ammonium nitrate

KW - Organocatalysis

KW - Phase transfer

KW - Reaction mechanisms

KW - Single electron transfer

UR - http://www.scopus.com/inward/record.url?scp=77956039300&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=77956039300&partnerID=8YFLogxK

U2 - 10.1002/anie.201001673

DO - 10.1002/anie.201001673

M3 - Article

C2 - 20632343

AN - SCOPUS:77956039300

SN - 1433-7851

VL - 49

SP - 6106

EP - 6110

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 35

ER -

Mechanistic complexity in organo-SOMO activation

Abstract

All Science Journal Classification (ASJC) codes

Keywords

Access to Document

Other files and links

Fingerprint

Cite this