Metal- and Acid-Free C-H Formylation of Nitrogen Heterocycles: Using Trioxane as an Aldehyde Equivalent Enabled by an Organic-Soluble Oxidant

被引：25

作者：

Ganley, Jacob M. ^{[1
,5
]}

Christensen, Melodie ^{[3
]}

Lam, Yu-hong ^{[4
]}

Peng, Zhengwei ^{[4
]}

Angeles, Angie R. ^{[2
,6
]}

Yeung, Charles S. ^{[1
]}

机构：

[1] Merck & Co Inc, Dept Discovery Chem, 33 Ave Louis Pasteur, Boston, MA 02115 USA

[2] Merck & Co Inc, Dept Proc Res & Dev, 33 Ave Louis Pasteur, Boston, MA 02115 USA

[3] Merck & Co Inc, Dept Proc Res & Dev, 90 East Scott Ave, Rahway, NJ 07065 USA

[4] Merck & Co Inc, Dept Modeling & Informat, 90 East Scott Ave, Rahway, NJ 07065 USA

[5] Princeton Univ, Dept Chem, Frick Chem Lab, Washington Rd, Princeton, NJ 08540 USA

[6] Gilead Sci, Dept Proc Chem, 333 Lakeside Dr, Foster City, CA 94404 USA

来源：

ORGANIC LETTERS | 2018年 / 20卷 / 18期

关键词：

DIRECT ALPHA-ARYLATION; PHOTOREDOX CATALYSIS; CARBONYLATION REACTIONS; ARYL HALIDES; BONDS; FUNCTIONALIZATION; HETEROARENES; ETHERS; MILD; HETEROARYLATION;

D O I：

10.1021/acs.orglett.8b02453

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A metal-free, innate, and practical C-H formylation of nitrogen heterocycles using trioxane as a formyl equivalent is reported. This reaction provides a mild and robust method for modifying medicinally relevant heterocycles with an aldehyde handle. The use of an organic soluble oxidant, tetrabutylammonium persulfate, is critical in promoting the desired coupling.

引用

页码：5752 / 5756

页数：5

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