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The phosphinoboration reaction.

Erika N Daley1, Christopher M Vogels, Stephen J Geier

  • 1Department of Chemistry and Biochemistry, Mount Allison University, 63C York Street, Sackville, New Brunswick, E4L 1G8 (Canada) http://thewildtoads.com/

Angewandte Chemie (International Ed. in English)
|January 6, 2015
PubMed
Summary
This summary is machine-generated.

Researchers synthesized phosphinoboronate esters with a single P-B bond. These compounds undergo addition reactions with various organic substrates, forming new P-C bonds and enabling novel synthetic pathways.

Keywords:
additionboroncatalysisphosphinesphosphinoboration

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Area of Science:

  • Organometallic Chemistry
  • Organic Synthesis
  • Boron Chemistry

Background:

  • Phosphinoboronate esters are versatile building blocks in organic synthesis.
  • The P-B bond offers unique reactivity for forming new carbon-phosphorus bonds.

Purpose of the Study:

  • To report the synthesis of phosphinoboronate esters featuring a single P-B bond.
  • To investigate the reactivity of these esters with diverse organic substrates.
  • To explore transition-metal-catalyzed phosphinoboration reactions.

Main Methods:

  • Synthesis of phosphinoboronate esters.
  • Addition reactions with aldehydes, ketones, aldimines, and enones.
  • Transition-metal-catalyzed phosphinoboration of allenes and alkynes.

Main Results:

  • Phosphinoboronate esters readily add to carbonyl compounds and imines, yielding 1,2-addition products with a new P-C bond.
  • The first transition-metal-catalyzed phosphinoborations of C-C multiple bonds were achieved in a single step.
  • Allenes undergo regioselective 1,2-addition, while terminal alkynes exhibit formal 1,1-addition.

Conclusions:

  • Phosphinoboronate esters are effective reagents for introducing phosphorus functionalities into organic molecules.
  • Transition-metal catalysis enables efficient P-C and B-C bond formation via phosphinoboration.
  • These findings expand the scope of organoboron and organophosphorus chemistry.