Tags

Type your tag names separated by a space and hit enter

trans-Hydroalkynylation of Internal 1,3-Enynes Enabled by Cooperative Catalysis.
J Am Chem Soc. 2023 Mar 15; 145(10):5624-5630.JA

Abstract

A cooperative catalyst system involving a Pd(0)/Senphos complex, tris(pentafluorophenyl)borane, copper bromide, and an amine base, is demonstrated to catalyze trans-hydroalkynylation of internal 1,3-enynes. For the first time, a Lewis acid catalyst is shown to promote the reaction involving the emerging outer-sphere oxidative reaction step. The resulting cross-conjugated dieneynes are versatile synthons for organic synthesis, and their characterization reveals distinct photophysical properties depending on the positioning of the donor/acceptor substituents along the conjugation path.

Authors+Show Affiliations

Department of Chemistry, Boston College, Chestnut Hill, Massachusetts 02467-3860, United States.Université de Pau et des Pays de l'Adour, E2S UPPA/CNRS, Institut des Sciences Analytiques et de Physico-Chimie pour l'Environnement et les Matériaux IPREM UMR 5254. Hélioparc, 2 Avenue P. Angot, 64053 Pau Cedex 09, France.Department of Chemistry, Boston College, Chestnut Hill, Massachusetts 02467-3860, United States.Department of Chemistry, Boston College, Chestnut Hill, Massachusetts 02467-3860, United States.Université de Pau et des Pays de l'Adour, E2S UPPA/CNRS, Institut des Sciences Analytiques et de Physico-Chimie pour l'Environnement et les Matériaux IPREM UMR 5254. Hélioparc, 2 Avenue P. Angot, 64053 Pau Cedex 09, France.Université de Pau et des Pays de l'Adour, E2S UPPA/CNRS, Institut des Sciences Analytiques et de Physico-Chimie pour l'Environnement et les Matériaux IPREM UMR 5254. Hélioparc, 2 Avenue P. Angot, 64053 Pau Cedex 09, France.Department of Chemistry, Boston College, Chestnut Hill, Massachusetts 02467-3860, United States. Université de Pau et des Pays de l'Adour, E2S UPPA/CNRS, Institut des Sciences Analytiques et de Physico-Chimie pour l'Environnement et les Matériaux IPREM UMR 5254. Hélioparc, 2 Avenue P. Angot, 64053 Pau Cedex 09, France.

Pub Type(s)

Journal Article

Language

eng

PubMed ID

36862947

Citation

Wang, Ziyong, et al. "Trans-Hydroalkynylation of Internal 1,3-Enynes Enabled By Cooperative Catalysis." Journal of the American Chemical Society, vol. 145, no. 10, 2023, pp. 5624-5630.
Wang Z, Zhang C, Wu J, et al. Trans-Hydroalkynylation of Internal 1,3-Enynes Enabled by Cooperative Catalysis. J Am Chem Soc. 2023;145(10):5624-5630.
Wang, Z., Zhang, C., Wu, J., Li, B., Chrostowska, A., Karamanis, P., & Liu, S. Y. (2023). Trans-Hydroalkynylation of Internal 1,3-Enynes Enabled by Cooperative Catalysis. Journal of the American Chemical Society, 145(10), 5624-5630. https://doi.org/10.1021/jacs.3c00514
Wang Z, et al. Trans-Hydroalkynylation of Internal 1,3-Enynes Enabled By Cooperative Catalysis. J Am Chem Soc. 2023 Mar 15;145(10):5624-5630. PubMed PMID: 36862947.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - trans-Hydroalkynylation of Internal 1,3-Enynes Enabled by Cooperative Catalysis. AU - Wang,Ziyong, AU - Zhang,Chen, AU - Wu,Jason, AU - Li,Bo, AU - Chrostowska,Anna, AU - Karamanis,Panaghiotis, AU - Liu,Shih-Yuan, Y1 - 2023/03/02/ PY - 2023/3/3/pubmed PY - 2023/3/3/medline PY - 2023/3/2/entrez SP - 5624 EP - 5630 JF - Journal of the American Chemical Society JO - J Am Chem Soc VL - 145 IS - 10 N2 - A cooperative catalyst system involving a Pd(0)/Senphos complex, tris(pentafluorophenyl)borane, copper bromide, and an amine base, is demonstrated to catalyze trans-hydroalkynylation of internal 1,3-enynes. For the first time, a Lewis acid catalyst is shown to promote the reaction involving the emerging outer-sphere oxidative reaction step. The resulting cross-conjugated dieneynes are versatile synthons for organic synthesis, and their characterization reveals distinct photophysical properties depending on the positioning of the donor/acceptor substituents along the conjugation path. SN - 1520-5126 UR - https://www.unboundmedicine.com/medline/citation/36862947/trans_Hydroalkynylation_of_Internal_13_Enynes_Enabled_by_Cooperative_Catalysis_ DB - PRIME DP - Unbound Medicine ER -
Try the Free App:
Prime PubMed app for iOS iPhone iPad
Prime PubMed app for Android
Prime PubMed is provided
free to individuals by:
Unbound Medicine.