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

78 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
Chemistry(all)
Biochemistry
Colloid and Surface Chemistry

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10.1021/jacs.7b01922

Cite this

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title = "Copper-Catalyzed Dicarbofunctionalization of Unactivated Olefins by Tandem Cyclization/Cross-Coupling",

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.",

author = "Surendra Thapa and Prakash Basnet and Ramesh Giri",

note = "Funding Information: We thank the University of New Mexico (UNM) and the National Science Foundation (NSF CHE-1554299) for financial support and for upgrades to the NMR (NSF grants CHE08-40523 and CHE09-46690) and MS facilities. The Bruker X-ray diffractometer was purchased via an NSF CRIF:MU award to UNM (CHE04-43580). Publisher Copyright: {\textcopyright} 2017 American Chemical Society.",

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N1 - Funding Information: We thank the University of New Mexico (UNM) and the National Science Foundation (NSF CHE-1554299) for financial support and for upgrades to the NMR (NSF grants CHE08-40523 and CHE09-46690) and MS facilities. The Bruker X-ray diffractometer was purchased via an NSF CRIF:MU award to UNM (CHE04-43580). Publisher Copyright: © 2017 American Chemical Society.

PY - 2017/4/26

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

Abstract

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