TiCl4-mediated deoxygenative reduction of aromatic ketones to alkylarenes with ammonia borane

被引：6

作者：

Zang, Yongjun ^{[1
]}

Ma, Yunfeng ^{[2
]}

Xu, Qilin ^{[1
]}

Li, Guosi ^{[1
]}

Chen, Naidong ^{[1
]}

Li, Xing ^{[3
]}

Zhu, Fucheng ^{[1
]}

机构：

[1] West Anhui Univ, Dept Biol & Pharmaceut Engn, Anhui Prov Key Lab Qual Evaluat & Improvement Trad, Luan 237012, Anhui, Peoples R China

[2] Anhui Anlito Biol Technol Co Ltd, Luan 237200, Anhui, Peoples R China

[3] Taizhou Univ, Coll Pharm & Chem & Chem Engn, Taizhou 225300, Jiangsu, Peoples R China

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2024年 / 22卷 / 05期

基金：

中国国家自然科学基金;

关键词：

SODIUM-BOROHYDRIDE; ARYL KETONES; ALDEHYDES; DISCOVERY; MILD; HYDROGENOLYSIS; HYDROGENATION; DIARYL; POTENT;

D O I：

10.1039/d3ob01977b

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A rapid and mild protocol for the exhaustive deoxygenation of various aromatic ketones to corresponding alkanes was described, which was mediated by TiCl4 and used ammonia borane (AB) as the reductant. This reduction protocol applies to a wide range of substrates in moderate to excellent yields at room temperature. The gram-scale reaction and syntheses of some key building blocks for SGLT2 inhibitors demonstrated the practicability of this methodology. Preliminary mechanistic studies revealed that the ketone is first converted into an alcohol, which then undergoes a carbocation to give the alkane via hydrogenolysis.

引用

页码：932 / 939

页数：8

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