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Carboxyboronate: A Versatile C1 Building Block.

Aleksandra Holownia1, Chieh-Hung Tien1, Diego B Diaz1

  • 1Davenport Research Laboratories, Department of Chemistry, University of Toronto, 80 St. George., Toronto, ON, M5S 3H6, Canada.

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|August 4, 2019
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Summary
This summary is machine-generated.

A new C1 building block, carboxy-MIDA-boronate, is synthesized and shows versatile reactivity. It enables access to novel borylated heterocycles and diverse bis(heteroaryl) compounds through Suzuki-Miyaura coupling and carbonylation reactions.

Keywords:
C1 building blockambident electrophilecarboxyboronatecross-couplingheterocycles

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Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry
  • Boron Chemistry

Background:

  • MIDA boronates are valuable synthetic intermediates.
  • Development of novel C1 building blocks is crucial for organic synthesis.
  • Efficient methods for constructing complex boron-containing heterocycles are in demand.

Purpose of the Study:

  • To describe the synthesis of carboxy-MIDA-boronate, a novel C1 building block.
  • To explore the reactivity and synthetic applications of carboxy-MIDA-boronate and its derivatives.
  • To demonstrate the utility of carboxy-MIDA-boronate in accessing borylated heterocycles and in carbonylation reactions.

Main Methods:

  • Ruthenium tetraoxide-mediated oxidative cleavage of ethynyl-MIDA-boronate to yield carboxy-MIDA-boronate.
  • Derivatization of the carboxylic acid group to form carbamoyl-, oxycarbo-, and thiocarboboronates.
  • Condensation reactions to form borylated heterocycles.
  • Suzuki-Miyaura cross-coupling reactions.
  • Palladium-catalyzed carbonylation reactions.

Main Results:

  • Carboxy-MIDA-boronate was successfully synthesized and characterized.
  • The molecule exhibits ambident reactivity towards nucleophiles.
  • A diverse range of previously unknown carbamoyl-, oxycarbo-, and thiocarboboronates were accessed.
  • Novel borylated heterocycles, including those with challenging boron substitution patterns, were synthesized.
  • The synthesized heterocycles were utilized in Suzuki-Miyaura coupling to form bis(heteroaryl) motifs.
  • The carbon monoxide-releasing capacity of carboxy-MIDA-boronate was demonstrated in palladium-catalyzed carbonylation.

Conclusions:

  • Carboxy-MIDA-boronate is a versatile C1 building block with broad synthetic utility.
  • Its derivatives and condensation products provide access to valuable borylated heterocycles.
  • This methodology facilitates the construction of complex molecules for applications in organic synthesis and materials science.