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^*

^*此作品的通讯作者

Yunnan Minzu University
Beijing Institute of Technology

科研成果: 期刊稿件 › 文章 › 同行评审

2 引用（Scopus）

摘要

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%).

源语言	英语
页（从-至）	3355-3360
页数	6
期刊	Organic Letters
卷	27
期	13
DOI	https://doi.org/10.1021/acs.orglett.5c00757
出版状态	已出版 - 4 4月 2025
已对外发布	是

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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",

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day = "4",

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

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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 - 2025/4/4

Y1 - 2025/4/4

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

VL - 27

SP - 3355

EP - 3360

JO - Organic Letters

JF - Organic Letters

IS - 13

ER -

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

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