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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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. |
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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 |
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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. |
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School of Physical and Mathematical Sciences |
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School of Physical and Mathematical Sciences Asako, Sobi Norinder, Jakob Llies, Laurean Yoshikai, Naohiko Nakamura, Eiichi |
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Article |
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Asako, Sobi Norinder, Jakob Llies, Laurean Yoshikai, Naohiko Nakamura, Eiichi |
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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 |
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2014 |
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https://hdl.handle.net/10356/101198 http://hdl.handle.net/10220/19715 |
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