Catalytic C-Alkylation of Pyrroles with Primary Alcohols: Hans Fischer's Alkali and a New Method with Iridium P,N,P-Pincer Complexes

被引：8

作者：

Koller, Sebastian ^{[1
,2
]}

Blazejak, Max ^{[1
,2
]}

Hintermann, Lukas ^{[1
,2
]}

机构：

[1] Tech Univ Munich, Dept Chem, Lichtenbergstr 4, D-85748 Garching, Germany

[2] TUM Catalysis Res Ctr, Ernst Otto Fischer Str 1, D-85748 Garching, Germany

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2018年 / 2018卷 / 14期

关键词：

Alkylation; Borrowing Hydrogen; Homogeneous catalysis; Iridium; Pyrrole; ALPHA-ALKYLATION; HYDROGEN AUTOTRANSFER; N-ALKYLATION; TRYPTAMINE DERIVATIVES; INDOLES; EFFICIENT; AMINES; DEHYDROGENATION; KETONES; ROUTE;

D O I：

10.1002/ejoc.201800146

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Hydrogen-autotransfer alkylation (HAT or "borrowing-hydrogen" alkylation) of heteroaromatic compounds has been studied with a range of substrates recently, but pyrroles have been largely absent from such studies. The conditions for HAT alkylations of pyrroles were investigated under a variety of conditions and were found to take place under basic alcoholic conditions (Hans Fischer alkylation) in the absence of transition-metal catalysts; by means of a heterogeneous Pd/C catalyst in the presence of base; and finally by means of homogeneous transition-metal catalysis combining a base and iridium pincer complexes generated in situ that have not previously been used in HAT alkylations of heterocycles.

引用

页码：1624 / 1633

页数：10

共 2 条

[1] Hydrogen bonds, coordination isomerism, and catalytic dehydrogenation of alcohols with the bifunctional iridium pincer complex (HOCH2)2(PCsp3P)\documentclass[12pt]{minimal} \usepackage{amsmath} \usepackage{wasysym} \usepackage{amsfonts} \usepackage{amssymb} \usepackage{amsbsy} \usepackage{mathrsfs} \usepackage{upgreek} \setlength{\oddsidemargin}{-69pt} \begin{document}$$^{{{\left( {HOC{H_2}} \right)}_2}}\left( {P{C_{s{p^3}}}P} \right)$$\end{document}IrHCl
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[2] Synthesis and characterization of new (N-diphenylphosphino)-isopropylanilines and their complexes: crystal structure of (Ph2P=S)NH-C6H4-4-CH(CH3)2 and catalytic activity of palladium(II) complexes in the Heck and Suzuki cross-coupling reactions
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APPLIED ORGANOMETALLIC CHEMISTRY, 2010, 24 (01) : 17 - 24

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