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Site-Selective and Stereoselective trans-Hydroboration of 1,3-Enynes Catalyzed by 1,4-Azaborine-Based Phosphine-Pd Complex.
J Am Chem Soc. 2016 11 09; 138(44):14566-14569.JA

Abstract

A concise synthesis of monobenzofused 1,4-azaborine phosphine ligands (Senphos) is described. These Senphos ligands uniquely support Pd-catalyzed trans-selective hydroboration of terminal and internal 1,3-enynes to furnish corresponding dienylboronates in high efficiency and diastereoselectivity. X-ray structural analysis of the Senphos-Pd(0) complex reveals a κ2-P-η2-BC coordination mode, and this isolated complex has been shown to serve as a competent catalyst for the trans-hydroboration reaction. This work demonstrates that the expanded chemical space provided by the BN/CC isosterism approach translates into the functional space in the context of stereoselective catalytic transformations.

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Authors+Show Affiliations

Xu S
Department of Chemistry, Boston College , Chestnut Hill, Massachusetts 02467-3860, United States.
Zhang Y
Department of Chemistry, Boston College , Chestnut Hill, Massachusetts 02467-3860, United States.
Li B
Department of Chemistry, Boston College , Chestnut Hill, Massachusetts 02467-3860, United States.
Liu SY
Department of Chemistry, Boston College , Chestnut Hill, Massachusetts 02467-3860, United States.

MeSH

AlkynesAzo CompoundsBoronCatalysisCoordination ComplexesLigandsMolecular StructurePalladiumPhosphines

Pub Type(s)

Journal Article
Research Support, N.I.H., Extramural
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

27802037

Citation

Xu, Senmiao, et al. "Site-Selective and Stereoselective trans-Hydroboration of 1,3-Enynes Catalyzed By 1,4-Azaborine-Based Phosphine-Pd Complex." Journal of the American Chemical Society, vol. 138, no. 44, 2016, pp. 14566-14569.
Xu S, Zhang Y, Li B, et al. Site-Selective and Stereoselective trans-Hydroboration of 1,3-Enynes Catalyzed by 1,4-Azaborine-Based Phosphine-Pd Complex. J Am Chem Soc. 2016;138(44):14566-14569.
Xu, S., Zhang, Y., Li, B., & Liu, S. Y. (2016). Site-Selective and Stereoselective trans-Hydroboration of 1,3-Enynes Catalyzed by 1,4-Azaborine-Based Phosphine-Pd Complex. Journal of the American Chemical Society, 138(44), 14566-14569.
Xu S, et al. Site-Selective and Stereoselective trans-Hydroboration of 1,3-Enynes Catalyzed By 1,4-Azaborine-Based Phosphine-Pd Complex. J Am Chem Soc. 2016 11 9;138(44):14566-14569. PubMed PMID: 27802037.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Site-Selective and Stereoselective trans-Hydroboration of 1,3-Enynes Catalyzed by 1,4-Azaborine-Based Phosphine-Pd Complex. AU - Xu,Senmiao, AU - Zhang,Yuanzhe, AU - Li,Bo, AU - Liu,Shih-Yuan, Y1 - 2016/11/01/ PY - 2016/11/2/pubmed PY - 2018/12/19/medline PY - 2016/11/2/entrez SP - 14566 EP - 14569 JF - Journal of the American Chemical Society JO - J Am Chem Soc VL - 138 IS - 44 N2 - A concise synthesis of monobenzofused 1,4-azaborine phosphine ligands (Senphos) is described. These Senphos ligands uniquely support Pd-catalyzed trans-selective hydroboration of terminal and internal 1,3-enynes to furnish corresponding dienylboronates in high efficiency and diastereoselectivity. X-ray structural analysis of the Senphos-Pd(0) complex reveals a κ2-P-η2-BC coordination mode, and this isolated complex has been shown to serve as a competent catalyst for the trans-hydroboration reaction. This work demonstrates that the expanded chemical space provided by the BN/CC isosterism approach translates into the functional space in the context of stereoselective catalytic transformations. SN - 1520-5126 UR - https://www.unboundmedicine.com/medline/citation/27802037/Site_Selective_and_Stereoselective_trans_Hydroboration_of_13_Enynes_Catalyzed_by_14_Azaborine_Based_Phosphine_Pd_Complex_ DB - PRIME DP - Unbound Medicine ER -