Communication
Nickel-Catalyzed Cross-Couplings of Organosilicon Reagents with Unactivated Secondary Alkyl Bromides
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Abstract

A metal-catalyzed cross-coupling of organosilicon compounds with alkyl halides has been developed. Noteworthy attributes of the method are its scope (secondary electrophiles), its high functional-group compatibility, and the air stability of the catalyst components.
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This article has been cited by 33 ACS Journal articles (5 most recent appear below).

Nickel-Catalyzed Enantioselective Cross-Couplings of Racemic Secondary Electrophiles That Bear an Oxygen Leaving Group
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Alexander J. Oelke, Jianwei Sun, and Gregory C. FuJournal of the American Chemical Society2012 Article ASAPTo date, effective nickel-catalyzed enantioselective cross-couplings of alkyl electrophiles that bear oxygen leaving groups have been limited to reactions of allylic alcohol derivatives with Grignard reagents. In this Communication, we establish that, in ...

Organozinc Chemistry Enabled by Micellar Catalysis. Palladium-Catalyzed Cross-Couplings between Alkyl and Aryl Bromides in Water at Room Temperature
Christophe Duplais, Arkady Krasovskiy, and Bruce H. LipshutzOrganometallics2011 30 (22), 6090-6097Organozinc Chemistry Enabled by Micellar Catalysis. Palladium-Catalyzed Cross-Couplings between Alkyl and Aryl Bromides in Water at Room Temperature
Christophe Duplais, Arkady Krasovskiy, and Bruce H. LipshutzOrganometallics2011 30 (22), 6090-6097Negishi-like cross-couplings between (functionalized) alkyl and aryl bromides are described. Despite the fact that organozinc reagents are intolerant of water, their formation as well as their use in an aqueous micellar environment is discussed herein. ...

Palladium-Catalyzed Hiyama Cross-Coupling of Aryltrifluorosilanes with Aryl and Heteroaryl Chlorides
Gary A. Molander and Laura IannazzoThe Journal of Organic Chemistry2011 76 (21), 9182-9187Palladium-Catalyzed Hiyama Cross-Coupling of Aryltrifluorosilanes with Aryl and Heteroaryl Chlorides
Gary A. Molander and Laura IannazzoThe Journal of Organic Chemistry2011 76 (21), 9182-9187An efficient, palladium-catalyzed Hiyama cross-coupling reaction of aryltrifluorosilanes with aryl chlorides has been developed. A wide variety of functionalized biaryl derivatives were isolated in good to excellent yields. The scope of this reaction has ...

Redox-Active Ligands and Organic Radical Chemistry
Di Zhu, Indira Thapa, Ilia Korobkov, Sandro Gambarotta, and Peter H. M. BudzelaarInorganic Chemistry2011 50 (20), 9879-9887Redox-Active Ligands and Organic Radical Chemistry
Di Zhu, Indira Thapa, Ilia Korobkov, Sandro Gambarotta, and Peter H. M. BudzelaarInorganic Chemistry2011 50 (20), 9879-9887Knowledge about bonding in diiminepyridine (L) halide, alkyl, and dinitrogen complexes of the metals iron, cobalt, and nickel is summarized, and two new examples are added to the set: L1Ni(Me) and L1Ni(N2). Reactivity of these types of complexes is ...

How Racemic Secondary Alkyl Electrophiles Proceed to Enantioselective Products in Negishi Cross-Coupling Reactions
Xufeng Lin, Jian Sun, Yanyan Xi, and Delian LinOrganometallics2011 Article ASAPHow Racemic Secondary Alkyl Electrophiles Proceed to Enantioselective Products in Negishi Cross-Coupling Reactions
Xufeng Lin, Jian Sun, Yanyan Xi, and Delian LinOrganometallics2011 Article ASAPTwo mechanisms, namely, the Ni(0)–Ni(II) and Ni(I)–Ni(III) mechanisms, for nickel-bis(oxazolinyl)pyridine complex catalyzed Negishi cross-coupling reaction were investigated with density functional calculations. The Ni(I)–Ni(III) mechanism, containing ...
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History
- Published In Issue June 30, 2004
- Received May 2, 2004
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