Palladium-Catalyzed Enantioselective Tandem Phosphinolation/Cyclization of ortho-Alkynylbenzaldehydes and H-Phosphine Oxides: Access to C1-Phosphinoylated 1H-Isochromenes

Linchun Zhang; Devendar Ponnam; Fan Yang; Meiqi Liang; Ruifeng Fan; Baomin Fan

doi:10.1021/acs.orglett.5c00757

Palladium-Catalyzed Enantioselective Tandem Phosphinolation/Cyclization of ortho-Alkynylbenzaldehydes and H-Phosphine Oxides: Access to C1-Phosphinoylated 1H-Isochromenes

Linchun Zhang, Devendar Ponnam, Fan Yang^*, Meiqi Liang, Ruifeng Fan^*, Baomin Fan^*

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

Abstract

A novel and effective method for the synthesis of chiral C1-phosphinoylated 1H-isochromenes has been developed. The reaction proceeds via a tandem asymmetric addition/cyclization under a catalytic system of Pd(OAc)₂, a Josiphos-based ligand L9, and ZnCl₂ in MeCN at 70 °C. This method demonstrates a broad substrate scope (27 examples), delivering excellent yields (up to 92%) and enantioselectivities (up to 95%).

Original language	English
Journal	Organic Letters
DOIs	https://doi.org/10.1021/acs.orglett.5c00757
Publication status	Accepted/In press - 2025
Externally published	Yes

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title = "Palladium-Catalyzed Enantioselective Tandem Phosphinolation/Cyclization of ortho-Alkynylbenzaldehydes and H-Phosphine Oxides: Access to C1-Phosphinoylated 1H-Isochromenes",

abstract = "A novel and effective method for the synthesis of chiral C1-phosphinoylated 1H-isochromenes has been developed. The reaction proceeds via a tandem asymmetric addition/cyclization under a catalytic system of Pd(OAc)2, a Josiphos-based ligand L9, and ZnCl2 in MeCN at 70 °C. This method demonstrates a broad substrate scope (27 examples), delivering excellent yields (up to 92\%) and enantioselectivities (up to 95\%).",

author = "Linchun Zhang and Devendar Ponnam and Fan Yang and Meiqi Liang and Ruifeng Fan and Baomin Fan",

note = "Publisher Copyright: {\textcopyright} 2025 American Chemical Society.",

year = "2025",

doi = "10.1021/acs.orglett.5c00757",

language = "English",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

}

TY - JOUR

T1 - Palladium-Catalyzed Enantioselective Tandem Phosphinolation/Cyclization of ortho-Alkynylbenzaldehydes and H-Phosphine Oxides

T2 - Access to C1-Phosphinoylated 1H-Isochromenes

AU - Zhang, Linchun

AU - Ponnam, Devendar

AU - Yang, Fan

AU - Liang, Meiqi

AU - Fan, Ruifeng

AU - Fan, Baomin

PY - 2025

Y1 - 2025

N2 - A novel and effective method for the synthesis of chiral C1-phosphinoylated 1H-isochromenes has been developed. The reaction proceeds via a tandem asymmetric addition/cyclization under a catalytic system of Pd(OAc)2, a Josiphos-based ligand L9, and ZnCl2 in MeCN at 70 °C. This method demonstrates a broad substrate scope (27 examples), delivering excellent yields (up to 92%) and enantioselectivities (up to 95%).

AB - A novel and effective method for the synthesis of chiral C1-phosphinoylated 1H-isochromenes has been developed. The reaction proceeds via a tandem asymmetric addition/cyclization under a catalytic system of Pd(OAc)2, a Josiphos-based ligand L9, and ZnCl2 in MeCN at 70 °C. This method demonstrates a broad substrate scope (27 examples), delivering excellent yields (up to 92%) and enantioselectivities (up to 95%).

UR - https://www.scopus.com/pages/publications/105000728276

U2 - 10.1021/acs.orglett.5c00757

DO - 10.1021/acs.orglett.5c00757

M3 - Article

AN - SCOPUS:105000728276

SN - 1523-7060

JO - Organic Letters

JF - Organic Letters

ER -

Palladium-Catalyzed Enantioselective Tandem Phosphinolation/Cyclization of ortho-Alkynylbenzaldehydes and H-Phosphine Oxides: Access to C1-Phosphinoylated 1H-Isochromenes

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