Cobalt(III)-Catalyzed Direct ortho-Alkenylation of Arylpyrazoles: A Comparative Study on Decarboxylation and Desilylation

Anil Kumar; Nachimuthu Muniraj; Kandikere Ramaiah Prabhu

doi:10.1002/ejoc.201900270

Cobalt(III)-Catalyzed Direct ortho-Alkenylation of Arylpyrazoles: A Comparative Study on Decarboxylation and Desilylation

Anil Kumar
, Nachimuthu Muniraj
, Kandikere Ramaiah Prabhu

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

11 Scopus citations

Abstract

A comparative study on Co ^III -catalyzed direct C–H bond alkenylation of 1-phenylpyrazole derivatives with alkynyl carboxylic acids and arylalkynylsilanes under redox-neutral conditions has been disclosed. These methods show excellent selectivity with good to excellent yields. Trimethylsilylacetylene has been utilized as a vinyl source to obtain the corresponding styrene derivatives. The major differences between these two reactions are the decarboxylation proceeds in the presence of a base additive whereas the desilylation takes place in the presence of an acid additive. The developed methodologies are compatible with a variety of functional groups.

Original language	English (US)
Pages (from-to)	2735-2739
Number of pages	5
Journal	European Journal of Organic Chemistry
Volume	2019
Issue number	16
DOIs	https://doi.org/10.1002/ejoc.201900270
State	Published - Apr 30 2019
Externally published	Yes

Keywords

Arylalkynyl carboxylic acids
Arylpyrazoles
Cobalt
C–H Activation
Earth-abundant metals

ASJC Scopus subject areas

Physical and Theoretical Chemistry
Organic Chemistry

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10.1002/ejoc.201900270

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title = "Cobalt(III)-Catalyzed Direct ortho-Alkenylation of Arylpyrazoles: A Comparative Study on Decarboxylation and Desilylation",

abstract = " A comparative study on Co III -catalyzed direct C–H bond alkenylation of 1-phenylpyrazole derivatives with alkynyl carboxylic acids and arylalkynylsilanes under redox-neutral conditions has been disclosed. These methods show excellent selectivity with good to excellent yields. Trimethylsilylacetylene has been utilized as a vinyl source to obtain the corresponding styrene derivatives. The major differences between these two reactions are the decarboxylation proceeds in the presence of a base additive whereas the desilylation takes place in the presence of an acid additive. The developed methodologies are compatible with a variety of functional groups.",

keywords = "Arylalkynyl carboxylic acids, Arylpyrazoles, Cobalt, C–H Activation, Earth-abundant metals",

author = "Anil Kumar and Nachimuthu Muniraj and Prabhu, \{Kandikere Ramaiah\}",

note = "Publisher Copyright: {\textcopyright} 2019 WILEY-VCH Verlag GmbH \& Co. KGaA, Weinheim",

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T1 - Cobalt(III)-Catalyzed Direct ortho-Alkenylation of Arylpyrazoles

T2 - A Comparative Study on Decarboxylation and Desilylation

AU - Kumar, Anil

AU - Muniraj, Nachimuthu

AU - Prabhu, Kandikere Ramaiah

PY - 2019/4/30

Y1 - 2019/4/30

N2 - A comparative study on Co III -catalyzed direct C–H bond alkenylation of 1-phenylpyrazole derivatives with alkynyl carboxylic acids and arylalkynylsilanes under redox-neutral conditions has been disclosed. These methods show excellent selectivity with good to excellent yields. Trimethylsilylacetylene has been utilized as a vinyl source to obtain the corresponding styrene derivatives. The major differences between these two reactions are the decarboxylation proceeds in the presence of a base additive whereas the desilylation takes place in the presence of an acid additive. The developed methodologies are compatible with a variety of functional groups.

AB - A comparative study on Co III -catalyzed direct C–H bond alkenylation of 1-phenylpyrazole derivatives with alkynyl carboxylic acids and arylalkynylsilanes under redox-neutral conditions has been disclosed. These methods show excellent selectivity with good to excellent yields. Trimethylsilylacetylene has been utilized as a vinyl source to obtain the corresponding styrene derivatives. The major differences between these two reactions are the decarboxylation proceeds in the presence of a base additive whereas the desilylation takes place in the presence of an acid additive. The developed methodologies are compatible with a variety of functional groups.

KW - Arylalkynyl carboxylic acids

KW - Arylpyrazoles

KW - Cobalt

KW - C–H Activation

KW - Earth-abundant metals

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UR - https://www.scopus.com/pages/publications/85065026600#tab=citedBy

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DO - 10.1002/ejoc.201900270

M3 - Article

AN - SCOPUS:85065026600

SN - 1434-193X

VL - 2019

SP - 2735

EP - 2739

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

IS - 16

ER -

Cobalt(III)-Catalyzed Direct ortho-Alkenylation of Arylpyrazoles: A Comparative Study on Decarboxylation and Desilylation

Abstract

Keywords

ASJC Scopus subject areas

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