Ortho-allylation of 1-arylpyrazoles with allyl phenyl ether via iron-catalyzed C-H bond activation under mild conditions

An iron salt and a bipyridine-type ligand catalyze the ortho-allylation of 1-arylpyrazoles and congeners with allyl phenyl ether under mild conditions (0 °C). The ligand, an organozinc base, and the nature of the allylating reagent are crucial for the success of this reaction. Under these conditions...

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Main Authors: Asako, Sobi, Norinder, Jakob, Llies, Laurean, Yoshikai, Naohiko, Nakamura, Eiichi
Other Authors: School of Physical and Mathematical Sciences
Format: Article
Language:English
Published: 2014
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Online Access:https://hdl.handle.net/10356/101198
http://hdl.handle.net/10220/19715
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Institution: Nanyang Technological University
Language: English
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spelling sg-ntu-dr.10356-1011982020-03-07T12:31:31Z Ortho-allylation of 1-arylpyrazoles with allyl phenyl ether via iron-catalyzed C-H bond activation under mild conditions Asako, Sobi Norinder, Jakob Llies, Laurean Yoshikai, Naohiko Nakamura, Eiichi School of Physical and Mathematical Sciences DRNTU::Science::Chemistry An iron salt and a bipyridine-type ligand catalyze the ortho-allylation of 1-arylpyrazoles and congeners with allyl phenyl ether under mild conditions (0 °C). The ligand, an organozinc base, and the nature of the allylating reagent are crucial for the success of this reaction. Under these conditions, a competitive phenylation reaction is largely retarded, and cross-coupling of the organozinc with the allyl electrophile is minimized. The reaction may proceed via iron-catalyzed ortho C[BOND]H activation to form a metallic intermediate, which then reacts with the allyl ether in a γ selective fashion. 2014-06-12T08:37:17Z 2019-12-06T20:35:07Z 2014-06-12T08:37:17Z 2019-12-06T20:35:07Z 2014 2014 Journal Article Asako, S., Norinder, J., Ilies, L., Yoshikai, N., & Nakamura, E. (2014). ortho -Allylation of 1-Arylpyrazoles with Allyl Phenyl Ether via Iron-Catalyzed C-H Bond Activation under Mild Conditions . Advanced Synthesis & Catalysis, 356(7), 1481-1485. 1615-4150 https://hdl.handle.net/10356/101198 http://hdl.handle.net/10220/19715 10.1002/adsc.201400063 en Advanced synthesis & catalysis © 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
institution Nanyang Technological University
building NTU Library
country Singapore
collection DR-NTU
language English
topic DRNTU::Science::Chemistry
spellingShingle DRNTU::Science::Chemistry
Asako, Sobi
Norinder, Jakob
Llies, Laurean
Yoshikai, Naohiko
Nakamura, Eiichi
Ortho-allylation of 1-arylpyrazoles with allyl phenyl ether via iron-catalyzed C-H bond activation under mild conditions
description An iron salt and a bipyridine-type ligand catalyze the ortho-allylation of 1-arylpyrazoles and congeners with allyl phenyl ether under mild conditions (0 °C). The ligand, an organozinc base, and the nature of the allylating reagent are crucial for the success of this reaction. Under these conditions, a competitive phenylation reaction is largely retarded, and cross-coupling of the organozinc with the allyl electrophile is minimized. The reaction may proceed via iron-catalyzed ortho C[BOND]H activation to form a metallic intermediate, which then reacts with the allyl ether in a γ selective fashion.
author2 School of Physical and Mathematical Sciences
author_facet School of Physical and Mathematical Sciences
Asako, Sobi
Norinder, Jakob
Llies, Laurean
Yoshikai, Naohiko
Nakamura, Eiichi
format Article
author Asako, Sobi
Norinder, Jakob
Llies, Laurean
Yoshikai, Naohiko
Nakamura, Eiichi
author_sort Asako, Sobi
title Ortho-allylation of 1-arylpyrazoles with allyl phenyl ether via iron-catalyzed C-H bond activation under mild conditions
title_short Ortho-allylation of 1-arylpyrazoles with allyl phenyl ether via iron-catalyzed C-H bond activation under mild conditions
title_full Ortho-allylation of 1-arylpyrazoles with allyl phenyl ether via iron-catalyzed C-H bond activation under mild conditions
title_fullStr Ortho-allylation of 1-arylpyrazoles with allyl phenyl ether via iron-catalyzed C-H bond activation under mild conditions
title_full_unstemmed Ortho-allylation of 1-arylpyrazoles with allyl phenyl ether via iron-catalyzed C-H bond activation under mild conditions
title_sort ortho-allylation of 1-arylpyrazoles with allyl phenyl ether via iron-catalyzed c-h bond activation under mild conditions
publishDate 2014
url https://hdl.handle.net/10356/101198
http://hdl.handle.net/10220/19715
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