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: | , , , , |
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| Other Authors: | |
| Format: | Article |
| Language: | English |
| Published: |
2014
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| Subjects: | |
| Online Access: | https://hdl.handle.net/10356/101198 http://hdl.handle.net/10220/19715 |
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| Institution: | Nanyang Technological University |
| Language: | English |
| Summary: | 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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