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铑(I)催化的吡啶和喹啉的直接芳基化反应。

Rh(I)-catalyzed direct arylation of pyridines and quinolines.

作者信息

Berman Ashley M, Lewis Jared C, Bergman Robert G, Ellman Jonathan A

机构信息

Department of Chemistry, University of California, Berkeley, California 94720, USA.

出版信息

J Am Chem Soc. 2008 Nov 12;130(45):14926-7. doi: 10.1021/ja8059396. Epub 2008 Oct 15.

DOI:10.1021/ja8059396
PMID:18855360
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC2647742/
Abstract

A Rh(I)-catalyzed direct arylation of pyridine and quinoline heterocycles has been developed. The method provides rapid entry into an important class of substituted heterocycles employing inexpensive and readily available starting materials.

摘要

已开发出一种铑(I)催化的吡啶和喹啉杂环的直接芳基化反应。该方法使用廉价且易于获得的起始原料,能够快速合成一类重要的取代杂环化合物。

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J Am Chem Soc. 2008 Jul 23;130(29):9254-6. doi: 10.1021/ja8026295. Epub 2008 Jun 27.
2
Rhodium-catalyzed regioselective C-H functionalization via decarbonylation of acid chlorides and C-H bond activation under phosphine-free conditions.铑催化的通过酰氯脱羰作用和在无膦条件下的C-H键活化实现的区域选择性C-H官能化反应。
J Am Chem Soc. 2008 Jul 2;130(26):8136-7. doi: 10.1021/ja803154h. Epub 2008 Jun 10.
3
A general and efficient method for the Suzuki-Miyaura coupling of 2-pyridyl nucleophiles.一种用于2-吡啶基亲核试剂的铃木-宫浦偶联反应的通用且高效的方法。
Angew Chem Int Ed Engl. 2008;47(25):4695-8. doi: 10.1002/anie.200801465.
4
Rh(I)-catalyzed arylation of heterocycles via C-H bond activation: expanded scope through mechanistic insight.通过C-H键活化实现铑(I)催化的杂环芳基化:基于机理洞察拓展反应范围
J Am Chem Soc. 2008 Feb 27;130(8):2493-500. doi: 10.1021/ja0748985. Epub 2008 Feb 2.
5
A strategy for C-H activation of pyridines: direct C-2 selective alkenylation of pyridines by nickel/Lewis acid catalysis.吡啶C-H活化的一种策略:通过镍/路易斯酸催化实现吡啶的直接C-2选择性烯基化反应。
J Am Chem Soc. 2008 Feb 27;130(8):2448-9. doi: 10.1021/ja710766j. Epub 2008 Feb 5.
6
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J Am Chem Soc. 2008 Jan 9;130(1):52-4. doi: 10.1021/ja710073n. Epub 2007 Dec 8.
7
Understanding the formation of N-H tautomers from alpha-substituted pyridines: tautomerization of 2-ethylpyridine promoted by osmium.理解α-取代吡啶中N-H互变异构体的形成:锇促进的2-乙基吡啶的互变异构化
J Am Chem Soc. 2007 Sep 12;129(36):10998-9. doi: 10.1021/ja073673r. Epub 2007 Aug 16.
8
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J Am Chem Soc. 2007 May 2;129(17):5332-3. doi: 10.1021/ja070388z. Epub 2007 Apr 6.
9
Aryl-aryl bond formation by transition-metal-catalyzed direct arylation.过渡金属催化直接芳基化形成芳基-芳基键。
Chem Rev. 2007 Jan;107(1):174-238. doi: 10.1021/cr0509760.
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Angew Chem Int Ed Engl. 2006 Nov 27;45(46):7781-6. doi: 10.1002/anie.200602773.