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Reilly MK, Rychnovsky SD. DABO Boronates: Stable Heterocyclic Boronic Acid Complexes for Use in Suzuki-Miyaura Cross-Coupling Reactions. Synlett. 2011;2011(16)doi: 10.1055/s-0030-1261218.
Reilly, M. K., & Rychnovsky, S. D. (2011). DABO Boronates: Stable Heterocyclic Boronic Acid Complexes for Use in Suzuki-Miyaura Cross-Coupling Reactions. Synlett : accounts and rapid communications in synthetic organic chemistry, 2011(16), . https://doi.org/10.1055/s-0030-1261218
Reilly, Maureen K, and Rychnovsky, Scott D. "DABO Boronates: Stable Heterocyclic Boronic Acid Complexes for Use in Suzuki-Miyaura Cross-Coupling Reactions." Synlett : accounts and rapid communications in synthetic organic chemistry vol. 2011,16 (2011). doi: https://doi.org/10.1055/s-0030-1261218
Reilly MK, Rychnovsky SD. DABO Boronates: Stable Heterocyclic Boronic Acid Complexes for Use in Suzuki-Miyaura Cross-Coupling Reactions. Synlett. 2011 Oct 01;2011(16). doi: 10.1055/s-0030-1261218. PMID: 24371372; PMCID: PMC3870905.
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Synlett. 2011 Oct 01;2011(16). doi: 10.1055/s-0030-1261218.

DABO Boronates: Stable Heterocyclic Boronic Acid Complexes for Use in Suzuki-Miyaura Cross-Coupling Reactions.

Synlett : accounts and rapid communications in synthetic organic chemistry

Maureen K Reilly, Scott D Rychnovsky

Affiliations

  1. 1102 NSII, Department of Chemistry, University of California, Irvine. Irvine, CA 92697-2025.

PMID: 24371372 PMCID: PMC3870905 DOI: 10.1055/s-0030-1261218

Abstract

Diethanolamine complexed heterocyclic boronic acids (DABO boronates) are air-stable reagents that can be used directly in Suzuki-Miyaura reactions in the presence of water or a protic co-solvent. Interestingly, heterocyclic DABO boronates can be stored for extended periods of time at room temperature with no noticeable degradation, unlike their boronic acid counterparts. Heterocyclic DABO boronates constitute an operationally simple and efficient alternative to other boronic acid derivatives as coupling partners in palladium catalyzed cross-coupling reactions under standard Suzuki-Miyaura conditions.

Keywords: Suzuki-Miyaura reaction; aryl boronate; cross-coupling; heterocyclic boronate; palladium catalysis

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