Selective Deuteration of Heterocycle N-Oxides via Iridium-Catalysed Hydrogen Isotope Exchange

被引：2

作者：

Owens, Philippa K. ^{[1
]}

Smith, Blair I. P. ^{[1
]}

Campos, Sebastien ^{[2
]}

Lindsay, David M. ^{[1
]}

Kerr, William J. ^{[1
]}

机构：

[1] Univ Strathclyde, Dept Pure & Appl Chem, Thomas Graham Bldg,295 Cathedral St, Glasgow City G1 1XL, Scotland

[2] GlaxoSmithKline R&D, Med Res Ctr, Stevenage SG1 2NY, England

来源：

SYNTHESIS-STUTTGART | 2023年 / 55卷 / 21期

基金：

英国工程与自然科学研究理事会;

关键词：

~iridium; catalysis; C-H activation; isotope labelling; quinolines; N-oxides; HIGHLY CHEMOSELECTIVE DEOXYGENATION; C-H FUNCTIONALIZATION; ACTIVATION; COMPLEXES; DEUTERIUM; ESTERS; MILD;

D O I：

10.1055/a-2088-4302

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An iridium(I) N-heterocyclic carbene/phosphine complex has been applied to the C-H activation and hydrogen isotope exchange of quinoline N-oxides. The isotope labelling proceeds under exceptionally low catalyst loadings of 0.25 mol% and delivers products with high levels of deuterium incorporation selectively at the C8 position. A broad substrate scope is demonstrated, with the method tolerant of electron-poor and -rich substrates, and of substitution adjacent to the site of CH activation. The isotope label is fully retained under standard deoxygenation conditions to give the corresponding labelled quinoline, and the labelling and deoxygenation can be combined in a one-pot procedure.

引用

页码：3644 / 3651

页数：8

共 22 条

[21] Site-Selective Nickel-Catalyzed Hydrogen Isotope Exchange in N-Heterocycles and Its Application to the Tritiation of Pharmaceuticals
Yang, Haifeng
Zarate, Cayetana
Palmer, W. Neil
Rivera, Nelo
Hesk, David
Chirik, Paul J.
ACS CATALYSIS, 2018, 8 (11): : 10210 - 10218
[22] C8-Selective Acylation of Quinoline N-Oxides with α-Oxocarboxylic Acids via Palladium-Catalyzed Regioselective C-H Bond Activation
Chen, Xiaopei
Cui, Xiuling
Wu, Yangjie
ORGANIC LETTERS, 2016, 18 (15) : 3722 - 3725

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