Copper-Catalyzed Dicarbofunctionalization of Unactivated Olefins by Tandem Cyclization/Cross-Coupling

Surendra Thapa; Prakash Basnet; Ramesh Giri

doi:10.1021/jacs.7b01922

Copper-Catalyzed Dicarbofunctionalization of Unactivated Olefins by Tandem Cyclization/Cross-Coupling

Surendra Thapa
, Prakash Basnet
, Ramesh Giri

Chemistry

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

94 Scopus citations

Abstract

We present a strategy that difunctionalizes unactivated olefins in 1,2-positions with two carbon-based entities. This method utilizes alkyl/arylzinc reagents derived from olefin-tethered alkyl/aryl halides that undergo radical cyclization to generate C(sp³)-Cu complexes in situ, which are intercepted with aryl and heteroaryl iodides. A variety of (arylmethyl)carbo- and heterocycles (N, O) can be synthesized with this new method.

Original language	English (US)
Pages (from-to)	5700-5703
Number of pages	4
Journal	Journal of the American Chemical Society
Volume	139
Issue number	16
DOIs	https://doi.org/10.1021/jacs.7b01922
State	Published - Apr 26 2017

All Science Journal Classification (ASJC) codes

Catalysis
General Chemistry
Biochemistry
Colloid and Surface Chemistry

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10.1021/jacs.7b01922

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abstract = "We present a strategy that difunctionalizes unactivated olefins in 1,2-positions with two carbon-based entities. This method utilizes alkyl/arylzinc reagents derived from olefin-tethered alkyl/aryl halides that undergo radical cyclization to generate C(sp3)-Cu complexes in situ, which are intercepted with aryl and heteroaryl iodides. A variety of (arylmethyl)carbo- and heterocycles (N, O) can be synthesized with this new method.",

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N2 - We present a strategy that difunctionalizes unactivated olefins in 1,2-positions with two carbon-based entities. This method utilizes alkyl/arylzinc reagents derived from olefin-tethered alkyl/aryl halides that undergo radical cyclization to generate C(sp3)-Cu complexes in situ, which are intercepted with aryl and heteroaryl iodides. A variety of (arylmethyl)carbo- and heterocycles (N, O) can be synthesized with this new method.

AB - We present a strategy that difunctionalizes unactivated olefins in 1,2-positions with two carbon-based entities. This method utilizes alkyl/arylzinc reagents derived from olefin-tethered alkyl/aryl halides that undergo radical cyclization to generate C(sp3)-Cu complexes in situ, which are intercepted with aryl and heteroaryl iodides. A variety of (arylmethyl)carbo- and heterocycles (N, O) can be synthesized with this new method.

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ER -

Copper-Catalyzed Dicarbofunctionalization of Unactivated Olefins by Tandem Cyclization/Cross-Coupling

Abstract

All Science Journal Classification (ASJC) codes

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