Iridium-catalysed ortho-H/D and -H/T exchange under basic conditions: C-H activation of unprotected tetrazoles

William J. Kerr; David M. Lindsay; Marc Reid; Jens Atzrodt; Volker Derdau; Patrick Rojahn; Remo Weck

doi:10.1039/C6CC02137A

Iridium-catalysed ortho-H/D and -H/T exchange under basic conditions: C-H activation of unprotected tetrazoles

William J. Kerr, David M. Lindsay, Marc Reid, Jens Atzrodt, Volker Derdau, Patrick Rojahn, Remo Weck

Pure And Applied Chemistry

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

58 Citations (Scopus)

182 Downloads (Pure)

Abstract

The first examples of selective ortho-directed C-H activation with unprotected 2-aryltetrazoles are described. A new base-assisted protocol for iridium (I) hydrogen isotope exchange catalysis allows access to ortho-deuterated and tritiated tetrazoles, including the tetrazole-containing pharmaceutical, Valsartan. Preliminary mechanistic studies are also presented.

Original language	English
Pages (from-to)	6669-6672
Number of pages	4
Journal	Chemical Communications
Volume	52
Issue number	40
Early online date	20 Apr 2016
DOIs	https://doi.org/10.1039/C6CC02137A
Publication status	E-pub ahead of print - 20 Apr 2016

Keywords

iridium (I) hydrogen isotope exchange catalysis
ortho-directed C-H activation
2-aryltetrazoles

Access to Document

10.1039/C6CC02137A

Kerr-etal-CC2016-Iridium-catalysed-ortho-HD-and-HT-exchange-under-basic-conditionsAccepted author manuscript, 4.04 MB

William Kerr
- w.kerrstrath.acuk
- Pure And Applied Chemistry - Professor
Person: Academic

Cite this

@article{db4843a2bec54a63bdf112319bf20c95,

title = "Iridium-catalysed ortho-H/D and -H/T exchange under basic conditions: C-H activation of unprotected tetrazoles",

abstract = "The first examples of selective ortho-directed C-H activation with unprotected 2-aryltetrazoles are described. A new base-assisted protocol for iridium (I) hydrogen isotope exchange catalysis allows access to ortho-deuterated and tritiated tetrazoles, including the tetrazole-containing pharmaceutical, Valsartan. Preliminary mechanistic studies are also presented.",

keywords = "iridium (I) hydrogen isotope exchange catalysis , ortho-directed C-H activation , 2-aryltetrazoles ",

author = "Kerr, {William J.} and Lindsay, {David M.} and Marc Reid and Jens Atzrodt and Volker Derdau and Patrick Rojahn and Remo Weck",

year = "2016",

month = apr,

day = "20",

doi = "10.1039/C6CC02137A",

language = "English",

volume = "52",

pages = "6669--6672",

journal = "Chemical Communications",

issn = "1359-7345",

publisher = "Royal Society of Chemistry",

number = "40",

}

TY - JOUR

T1 - Iridium-catalysed ortho-H/D and -H/T exchange under basic conditions

T2 - C-H activation of unprotected tetrazoles

AU - Kerr, William J.

AU - Lindsay, David M.

AU - Reid, Marc

AU - Atzrodt, Jens

AU - Derdau, Volker

AU - Rojahn, Patrick

AU - Weck, Remo

PY - 2016/4/20

Y1 - 2016/4/20

N2 - The first examples of selective ortho-directed C-H activation with unprotected 2-aryltetrazoles are described. A new base-assisted protocol for iridium (I) hydrogen isotope exchange catalysis allows access to ortho-deuterated and tritiated tetrazoles, including the tetrazole-containing pharmaceutical, Valsartan. Preliminary mechanistic studies are also presented.

AB - The first examples of selective ortho-directed C-H activation with unprotected 2-aryltetrazoles are described. A new base-assisted protocol for iridium (I) hydrogen isotope exchange catalysis allows access to ortho-deuterated and tritiated tetrazoles, including the tetrazole-containing pharmaceutical, Valsartan. Preliminary mechanistic studies are also presented.

KW - iridium (I) hydrogen isotope exchange catalysis

KW - ortho-directed C-H activation

KW - 2-aryltetrazoles

U2 - 10.1039/C6CC02137A

DO - 10.1039/C6CC02137A

M3 - Article

VL - 52

SP - 6669

EP - 6672

JO - Chemical Communications

JF - Chemical Communications

SN - 1359-7345

IS - 40

ER -

Iridium-catalysed ortho-H/D and -H/T exchange under basic conditions: C-H activation of unprotected tetrazoles

Abstract

Keywords

Access to Document

Fingerprint

Profiles

William Kerr

Cite this