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Copper-catalyzed β-boration of α,β-unsaturated carbonyl compounds with tetrahydroxydiborane.
Org Lett. 2011 Sep 02; 13(17):4684-7.OL

Abstract

The copper-catalyzed β-boration of α,β-unsaturated carbonyl compounds with tetrahydroxydiborane has been developed. This diboron reagent allows direct, efficient access to boronic acids and their derivatives. Primary, secondary, and tertiary α,β-unsaturated amides are converted to the corresponding β-trifluoroboratoamides in good to excellent yields. The β-boration of a variety of α,β-unsaturated esters and ketones is also reported.

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Authors+Show Affiliations

Molander GA
Roy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania 19104-6323, USA. gmolandr@sas.upenn.edu
McKee SA
No affiliation info available

MeSH

Boron CompoundsCatalysisCopperKetonesMolecular StructureStereoisomerism

Pub Type(s)

Journal Article
Research Support, N.I.H., Extramural

Language

eng

PubMed ID

21819097

Citation

Molander, Gary A., and Silas A. McKee. "Copper-catalyzed Β-boration of Α,β-unsaturated Carbonyl Compounds With Tetrahydroxydiborane." Organic Letters, vol. 13, no. 17, 2011, pp. 4684-7.
Molander GA, McKee SA. Copper-catalyzed β-boration of α,β-unsaturated carbonyl compounds with tetrahydroxydiborane. Org Lett. 2011;13(17):4684-7.
Molander, G. A., & McKee, S. A. (2011). Copper-catalyzed β-boration of α,β-unsaturated carbonyl compounds with tetrahydroxydiborane. Organic Letters, 13(17), 4684-7. https://doi.org/10.1021/ol201900d
Molander GA, McKee SA. Copper-catalyzed Β-boration of Α,β-unsaturated Carbonyl Compounds With Tetrahydroxydiborane. Org Lett. 2011 Sep 2;13(17):4684-7. PubMed PMID: 21819097.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Copper-catalyzed β-boration of α,β-unsaturated carbonyl compounds with tetrahydroxydiborane. AU - Molander,Gary A, AU - McKee,Silas A, Y1 - 2011/08/05/ PY - 2011/8/9/entrez PY - 2011/8/9/pubmed PY - 2011/12/13/medline SP - 4684 EP - 7 JF - Organic letters JO - Org Lett VL - 13 IS - 17 N2 - The copper-catalyzed β-boration of α,β-unsaturated carbonyl compounds with tetrahydroxydiborane has been developed. This diboron reagent allows direct, efficient access to boronic acids and their derivatives. Primary, secondary, and tertiary α,β-unsaturated amides are converted to the corresponding β-trifluoroboratoamides in good to excellent yields. The β-boration of a variety of α,β-unsaturated esters and ketones is also reported. SN - 1523-7052 UR - https://www.unboundmedicine.com/medline/citation/21819097/Copper_catalyzed_β_boration_of_αβ_unsaturated_carbonyl_compounds_with_tetrahydroxydiborane_ L2 - https://doi.org/10.1021/ol201900d DB - PRIME DP - Unbound Medicine ER -