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Palladium-Catalyzed Asymmetric Intramolecular Dearomative Heck Annulation of Aryl Halides to Furnish Indolines.
J Org Chem. 2021 Nov 05; 86(21):14640-14651.JO

Abstract

An unprecedented Pd-catalyzed asymmetric intramolecular cascade cyclization of aryl halides with readily available arylboronic acids proceeds through a Heck-type dearomative cyclization terminated with arylation in the presence of Pd2(dba)3 (10 mol %), Cu2O (5 mol %), and Cs2CO3 (2.0 equiv) in 1,2-dichloroethane (1.0 mL) at 100 °C for 15 h in air using BINOL-based phosphoramidite as the chiral ligand. This dearomative Heck protocol, which tolerates a broad variety of functional groups, is amenable to the generation of optically active indoline derivatives bearing all-carbon quaternary stereogenic centers in one step in moderate to excellent yields, with excellent diastereoselectivities (>20:1) and enantioselectivities (up to >99% ee). It is worth mentioning that no decrease in the enantiopurity of the indoline derivatives was observed during the synthetic transformations of the products.

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Publisher Full Text (DOI)

Authors+Show Affiliations

School of Chemical Engineering and Technology, Hebei University of Technology, Tianjin 300130, People's Republic of China.

School of Chemical Engineering and Technology, Hebei University of Technology, Tianjin 300130, People's Republic of China.

School of Chemical Engineering and Technology, Hebei University of Technology, Tianjin 300130, People's Republic of China.

School of Chemical Engineering and Technology, Hebei University of Technology, Tianjin 300130, People's Republic of China.

School of Chemical Engineering and Technology, Hebei University of Technology, Tianjin 300130, People's Republic of China.

State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, People's Republic of China.

Pub Type(s)

Journal Article

Language

eng

PubMed ID

34645261

Citation

Li, Yuanfeng, et al. "Palladium-Catalyzed Asymmetric Intramolecular Dearomative Heck Annulation of Aryl Halides to Furnish Indolines." The Journal of Organic Chemistry, vol. 86, no. 21, 2021, pp. 14640-14651.

Li Y, Zhang HY, Zhang Y, et al. Palladium-Catalyzed Asymmetric Intramolecular Dearomative Heck Annulation of Aryl Halides to Furnish Indolines. J Org Chem. 2021;86(21):14640-14651.

Li, Y., Zhang, H. Y., Zhang, Y., Han, Y. P., Zhao, J., & Liang, Y. M. (2021). Palladium-Catalyzed Asymmetric Intramolecular Dearomative Heck Annulation of Aryl Halides to Furnish Indolines. The Journal of Organic Chemistry, 86(21), 14640-14651. https://doi.org/10.1021/acs.joc.1c01478

Li Y, et al. Palladium-Catalyzed Asymmetric Intramolecular Dearomative Heck Annulation of Aryl Halides to Furnish Indolines. J Org Chem. 2021 Nov 5;86(21):14640-14651. PubMed PMID: 34645261.

* Article titles in AMA citation format should be in sentence-case

TY - JOUR T1 - Palladium-Catalyzed Asymmetric Intramolecular Dearomative Heck Annulation of Aryl Halides to Furnish Indolines. AU - Li,Yuanfeng, AU - Zhang,Hong-Yu, AU - Zhang,Yuecheng, AU - Han,Ya-Ping, AU - Zhao,Jiquan, AU - Liang,Yong-Min, Y1 - 2021/10/14/ PY - 2021/10/15/pubmed PY - 2021/10/15/medline PY - 2021/10/14/entrez SP - 14640 EP - 14651 JF - The Journal of organic chemistry JO - J Org Chem VL - 86 IS - 21 N2 - An unprecedented Pd-catalyzed asymmetric intramolecular cascade cyclization of aryl halides with readily available arylboronic acids proceeds through a Heck-type dearomative cyclization terminated with arylation in the presence of Pd2(dba)3 (10 mol %), Cu2O (5 mol %), and Cs2CO3 (2.0 equiv) in 1,2-dichloroethane (1.0 mL) at 100 °C for 15 h in air using BINOL-based phosphoramidite as the chiral ligand. This dearomative Heck protocol, which tolerates a broad variety of functional groups, is amenable to the generation of optically active indoline derivatives bearing all-carbon quaternary stereogenic centers in one step in moderate to excellent yields, with excellent diastereoselectivities (>20:1) and enantioselectivities (up to >99% ee). It is worth mentioning that no decrease in the enantiopurity of the indoline derivatives was observed during the synthetic transformations of the products. SN - 1520-6904 UR - https://www.unboundmedicine.com/medline/citation/34645261/Palladium_Catalyzed_Asymmetric_Intramolecular_Dearomative_Heck_Annulation_of_Aryl_Halides_to_Furnish_Indolines_ DB - PRIME DP - Unbound Medicine ER -