Catalyst-dependent chemoselective insertion of diazoalkanes into the N-H/C-H/O-H/C-O bonds of 2-hydroxybenzothiazoles

被引：11

作者：

Jin, Lvnan ^{[1
]}

Zhou, Xuan ^{[1
]}

Zhao, Yunbo ^{[1
]}

Guo, Jing ^{[1
]}

Stephan, Douglas W. ^{[2
]}

机构：

[1] Ningbo Univ, Inst Drug Discovery Technol, Ningbo 315211, Zhejiang, Peoples R China

[2] Univ Toronto, Dept Chem, 80 St George St, Toronto, ON M5S 3H6, Canada

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2022年 / 20卷 / 39期

关键词：

ORGANIC-SYNTHESIS; DIAZO-COMPOUNDS; METAL CARBENE; H INSERTION; BENZOTHIAZOLONE; DIAZOESTERS; ALKYLATION; INHIBITORS; DESIGN;

D O I：

10.1039/d2ob01048h

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The control of chemoselective insertions of diazoalkanes into 2-hydroxybenzothiazoles is challenging. Herein, the chemoselective N-H, O-H, C-O or C-H bond insertions of diazoalkanes into 2-hydroxybenzothiazoles are achieved using B(C6F5)(3), Rh-2(OAc)(4) or TfOH as the catalyst. This affords routes to 54 benzothiazole derivatives. These protocols are scalable and demonstrate the complementary nature of Lewis acid, transition metal and Bronsted acid catalyses.

引用

页码：7781 / +

页数：7

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