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Allenylation and propargylation reactions of ketones, aldehydes, imines, and iminium ions using organoboronates and related derivatives

Journal Article


Abstract


  • Allenyl- and propargylboronates have emerged as versatile reagents to effect regioselective propargylation or allenylation reactions of aldehydes, ketones, imines, and iminium ions. These boron-derived reagents have the ability to undergo transmetalation reactions with other metals (Ag, Cu, In, and Zn), often using only catalytic amounts of these metals, leading to more facile and highly regioselective reactions. Enantioselective organocatalyzed reactions have also been developed using, chiral diols, aminophenols, and phosphoric acids. This short review highlights recent developments in this area.

Publication Date


  • 2017

Citation


  • Thaima, T., Zamani, F., Hyland, C. J. T. & Pyne, S. G. (2017). Allenylation and propargylation reactions of ketones, aldehydes, imines, and iminium ions using organoboronates and related derivatives. Synthesis (Germany), 49 (7), 1461-1480.

Scopus Eid


  • 2-s2.0-85010004765

Number Of Pages


  • 19

Start Page


  • 1461

End Page


  • 1480

Volume


  • 49

Issue


  • 7

Abstract


  • Allenyl- and propargylboronates have emerged as versatile reagents to effect regioselective propargylation or allenylation reactions of aldehydes, ketones, imines, and iminium ions. These boron-derived reagents have the ability to undergo transmetalation reactions with other metals (Ag, Cu, In, and Zn), often using only catalytic amounts of these metals, leading to more facile and highly regioselective reactions. Enantioselective organocatalyzed reactions have also been developed using, chiral diols, aminophenols, and phosphoric acids. This short review highlights recent developments in this area.

Publication Date


  • 2017

Citation


  • Thaima, T., Zamani, F., Hyland, C. J. T. & Pyne, S. G. (2017). Allenylation and propargylation reactions of ketones, aldehydes, imines, and iminium ions using organoboronates and related derivatives. Synthesis (Germany), 49 (7), 1461-1480.

Scopus Eid


  • 2-s2.0-85010004765

Number Of Pages


  • 19

Start Page


  • 1461

End Page


  • 1480

Volume


  • 49

Issue


  • 7