Rh(III)-Catalyzed Regioselective Alkyne Insertion in the Context of C-H Activation and Lactonization Reactions: Synthesis of Fused 1,2-Oxaphospholenes

被引：1

作者：

Yang, Yingying ^{[1
]}

Chen, Menghan ^{[1
]}

Xuan, Qingqing ^{[1
]}

Xu, Jian ^{[1
]}

Song, Qiuling ^{[1
,2
,3
]}

机构：

[1] Huaqiao Univ, Inst Next Generat Matter Transformat, Coll Mat Sci Engn, Xiamen 361021, Fujian, Peoples R China

[2] Fujian Prov Univ, Fuzhou Univ, Key Lab Mol Synth & Funct Discovery, Coll Chem, Fuzhou 350108, Fujian, Peoples R China

[3] Henan Normal Univ, Sch Chem & Chem Engn, Xinxiang 453007, Henan, Peoples R China

来源：

ORGANIC LETTERS | 2024年 / 26卷 / 36期

基金：

中国国家自然科学基金;

关键词：

1,2-ALLENYL PHOSPHONIC-ACIDS; CYCLIC PHOSPHATIDIC-ACID; LYSOPHOSPHATIDIC ACID; CYCLIZATION; INHIBITION; MONOESTERS; ANALOGS; PHYLPA;

D O I：

10.1021/acs.orglett.4c02794

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Herein, we report an expedient synthesis of fused phosphorus-containing heterocycles via Rh-catalyzed cascade C-H activation, alkyne insertion, and lactonization reactions. The substrate scope and the group tolerance are good, as various substituted benzoic acids, N-methoxybenzamides, and 2-phenylindoles could go through the reactions smoothly to afford the corresponding products in moderate to high yields. Additionally, excellent regioselectivities are shown in the alkyne insertion with the assistance of an electron-withdrawing phosphonate group.

引用

页码：7683 / 7687

页数：5

共 32 条

[21] Synthesis of 3-(arylamino)-5-bromo-2-phenyl-2,3-dihydro-25-benzo[d][1,2]-oxaphosphol-2-oxides [J].

Prasad, G. Syam ;

Babu, B. Hari ;

Raju, C. Naga ;

Reddy, C. Devendranath ;

Reddy, C. Suresh .

SYNTHETIC COMMUNICATIONS, 2009, 39 (07) :1310-1316

[22] Phosphorothioate analogues of alkyl lysophosphaticlic acid as LPA3 receptor-selective agonists [J].

Qian, Lian ;

Xu, Yong ;

Simper, Ted ;

Jiang, Guowei ;

Aoki, Junken ;

Umezu-Goto, Makiko ;

Arai, Hiroyuki ;

Yu, Shuangxing ;

Mills, Gordon B. ;

Tsukahara, Ryoko ;

Makarova, Natalia ;

Fujiwara, Yuko ;

Tigyi, Gabor ;

Prestwich, Glenn D. .

CHEMMEDCHEM, 2006, 1 (03) :376-383

[23] Rhodium(III)-Catalyzed Enantiotopic C-HActivation Enables Access to P-Chiral Cyclic Phosphinamides [J].

Sun, Yang ;

Cramer, Nicolai .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (01) :364-367

[24] Rhodium(III)-catalyzed Oxidative Coupling through C-H Bond Cleavage Directed by Phosphinoxy Groups [J].

Unoh, Yuto ;

Hashimoto, Yuto ;

Takeda, Daisuke ;

Hirano, Koji ;

Satoh, Tetsuya ;

Miura, Masahiro .

ORGANIC LETTERS, 2013, 15 (13) :3258-3261

[25] Recent advances in the Rh-catalyzed cascade arene C-H bond activation/annulation toward diverse heterocyclic compounds [J].

Wang, Chang ;

Chen, Fan ;

Qian, Pengcheng ;

Cheng, Jiang .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2021, 19 (08) :1705-1721

[26] Phosphonothioate and fluoromethylene phosphonate analogues of cyclic phosphatidic acid: Novel antagonists of lysophosphatidic acid receptors [J].

Xu, Yong ;

Jiang, Guowei ;

Tsukahara, Ryoko ;

Fujiwara, Yuko ;

Tigyi, Gabor ;

Prestwich, Glenn D. .

JOURNAL OF MEDICINAL CHEMISTRY, 2006, 49 (17) :5309-5315

[27] One-Pot Synthesis of Fused N,O-Heterocycles through Rh(III)-Catalyzed Cascade Reactions of Aromatic/Vinylic N-Alkoxy-Amides with 4-Hydroxy-2-Alkynoates [J].

Xu, Yuanshuang ;

Li, Bin ;

Zhang, Xinying ;

Fan, Xuesen .

ADVANCED SYNTHESIS & CATALYSIS, 2018, 360 (14) :2613-2620

[28] Pd-catalyzed regio- and stereoselective cyclization-Heck reaction of monoesters of 1,2-allenyl phosphonic acids with alkenes [J].

Yu, Fei ;

Lian, Xiongdong ;

Ma, Shengming .

ORGANIC LETTERS, 2007, 9 (09) :1703-1706

[29] CuX2-Mediated Halolactonization Reaction of Monoesters of 1,2-Allenyl Phosphonic Acids and Their Suzuki Cross-Coupling Reaction [J].

Yu, Fei ;

Lian, Xiongdong ;

Zhao, Jinbo ;

Yu, Yihua ;

Ma, Shengming .

JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (03) :1130-1134

[30] Transition-metal-catalyzed aromatic C-H functionalization assisted by the phosphorus-containing directing groups [J].

Zhang, Jian ;

Yao, Lingyun ;

Su, Jia-Yi ;

Liu, Yang-Zi ;

Wang, Quannan ;

Deng, Wei Ping .

GREEN SYNTHESIS AND CATALYSIS, 2023, 4 (03) :206-225

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