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Title: Nickel-catalyzed difunctionalization of allyl moieties using organoboronic acids and halides with divergent regioselectivities
Authors: Li, W 
Boon, J.K
Zhao, Y 
Keywords: Catalysis
Building blockes
Mechanistic studies
Molecular complexity
Organic halides
Organic synthesis
Organoboronic acids
Rapid construction
Issue Date: 2018
Publisher: Royal Society of Chemistry
Citation: Li, W, Boon, J.K, Zhao, Y (2018). Nickel-catalyzed difunctionalization of allyl moieties using organoboronic acids and halides with divergent regioselectivities. Chemical Science 9 (3) : 600-607. ScholarBank@NUS Repository.
Abstract: Efficient difunctionalization of alkenes allows the rapid construction of molecular complexity from simple building blocks in organic synthesis. We present herein a nickel-catalyzed dicarbofunctionalization of alkenes using readily available organoboronic acids and organic halides in a three-component fashion. In particular, an unprecedented regioselectivity of the 1,3-dicarbofunctionalization of N-allylpyrimidin-2-amine is achieved when aryl and methyl iodides are utilized. In contrast, the use of alkyl bromides with ?-hydrogens results in 1,3-hydroarylation or oxidative 1,3-diarylation. Preliminary mechanistic studies suggest an isomerization involving nickel hydride in the 1,3-difunctionalization reactions. On the other hand, the use of alkenyl or alkynyl halides promotes alternative regioselectivities to deliver 1,2-alkenylcarbonation or intriguing 2,1-alkynylcarbonation products. Such 2,1-alkynylarylation is also applicable to N-allylbenzamide as a different class of substrates. Overall, this nickel-catalyzed process proves to be powerful in delivering versatile difunctionalized compounds using readily available reagents/catalysts and a simple procedure. © 2018 The Royal Society of Chemistry.
Source Title: Chemical Science
ISSN: 2041-6520
DOI: 10.1039/c7sc03149a
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