Catalyst-Switchable Regiocontrol in the Direct Arylation of Remote C—H Groups in Pyrazolo[1,5-a]pyrimidines

Robin B Bedford; Steven J Durrant; Michelle Montgomery

doi:10.1002/anie.201502150

Catalyst-Switchable Regiocontrol in the Direct Arylation of Remote C—H Groups in Pyrazolo[1,5-a]pyrimidines

Robin B Bedford, Steven J Durrant, Michelle Montgomery

Research output: Contribution to journal › Article (Academic Journal) › peer-review

45 Citations (Scopus)

363 Downloads (Pure)

Abstract

The regiodivergent palladium-catalyzed CH arylation of pyrazolo[1,5-a]pyrimidine has been achieved, wherein the switch in regioselectivity between positions C3 and C7 is under complete catalyst control. A phosphine-containing palladium catalyst promotes the direct arylation at the most acidic position (C7), whereas a phosphine-free catalyst targets the most electron-rich position (C3).

Original language	English
Pages (from-to)	8787-8790
Number of pages	4
Journal	Angewandte Chemie - International Edition
Volume	54
Issue number	30
Early online date	10 Jun 2015
DOIs	https://doi.org/10.1002/anie.201502150
Publication status	Published - 20 Jul 2015

Structured keywords

BCS and TECS CDTs

Keywords

arylation
C—H activation
palladium
regiocontrol

Access to Document

10.1002/anie.201502150Licence: CC BY

Bedford et al 2015 Angewandte Chemie International Edition
©2015 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the Creative Commons Attribution License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.
Final published version, 853 KBLicence: CC BY

1 Finished

3-month Core Capability for Chemistry Research
Crosby, J.
1/01/13 → 1/04/13
Project: Research

Professor Robin B Bedford
- School of Chemistry - Professor of Catalysis
- Synthesis
- Supramolecular and Mechanistic Chemistry
- Catalysis
Person: Academic , Member

Cite this

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title = "Catalyst-Switchable Regiocontrol in the Direct Arylation of Remote C—H Groups in Pyrazolo[1,5-a]pyrimidines",

abstract = "The regiodivergent palladium-catalyzed CH arylation of pyrazolo[1,5-a]pyrimidine has been achieved, wherein the switch in regioselectivity between positions C3 and C7 is under complete catalyst control. A phosphine-containing palladium catalyst promotes the direct arylation at the most acidic position (C7), whereas a phosphine-free catalyst targets the most electron-rich position (C3).",

keywords = "arylation, C—H activation, palladium, regiocontrol",

author = "Bedford, {Robin B} and Durrant, {Steven J} and Michelle Montgomery",

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T1 - Catalyst-Switchable Regiocontrol in the Direct Arylation of Remote C—H Groups in Pyrazolo[1,5-a]pyrimidines

AU - Bedford, Robin B

AU - Durrant, Steven J

AU - Montgomery, Michelle

PY - 2015/7/20

Y1 - 2015/7/20

N2 - The regiodivergent palladium-catalyzed CH arylation of pyrazolo[1,5-a]pyrimidine has been achieved, wherein the switch in regioselectivity between positions C3 and C7 is under complete catalyst control. A phosphine-containing palladium catalyst promotes the direct arylation at the most acidic position (C7), whereas a phosphine-free catalyst targets the most electron-rich position (C3).

AB - The regiodivergent palladium-catalyzed CH arylation of pyrazolo[1,5-a]pyrimidine has been achieved, wherein the switch in regioselectivity between positions C3 and C7 is under complete catalyst control. A phosphine-containing palladium catalyst promotes the direct arylation at the most acidic position (C7), whereas a phosphine-free catalyst targets the most electron-rich position (C3).

KW - arylation

KW - C—H activation

KW - palladium

KW - regiocontrol

U2 - 10.1002/anie.201502150

DO - 10.1002/anie.201502150

M3 - Article (Academic Journal)

C2 - 26095315

VL - 54

SP - 8787

EP - 8790

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

SN - 1433-7851

IS - 30

ER -

Catalyst-Switchable Regiocontrol in the Direct Arylation of Remote C—H Groups in Pyrazolo[1,5-a]pyrimidines

Abstract

Structured keywords

Keywords

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Professor Robin B Bedford

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