scispace - formally typeset
Topic

Aryl

About: Aryl is a(n) research topic. Over the lifetime, 95605 publication(s) have been published within this topic receiving 1376401 citation(s). The topic is also known as: aryl group.
Papers
More filters


Journal ArticleDOI
10 Jan 2007-Chemical Reviews
TL;DR: A number of improvements have developed the former process into an industrially very useful and attractive method for the construction of aryl -aryl bonds, but the need still exists for more efficient routes whereby the same outcome is accomplished, but with reduced waste and in fewer steps.
Abstract: The biaryl structural motif is a predominant feature in many pharmaceutically relevant and biologically active compounds. As a result, for over a century 1 organic chemists have sought to develop new and more efficient aryl -aryl bond-forming methods. Although there exist a variety of routes for the construction of aryl -aryl bonds, arguably the most common method is through the use of transition-metalmediated reactions. 2-4 While earlier reports focused on the use of stoichiometric quantities of a transition metal to carry out the desired transformation, modern methods of transitionmetal-catalyzed aryl -aryl coupling have focused on the development of high-yielding reactions achieved with excellent selectivity and high functional group tolerance under mild reaction conditions. Typically, these reactions involve either the coupling of an aryl halide or pseudohalide with an organometallic reagent (Scheme 1), or the homocoupling of two aryl halides or two organometallic reagents. Although a number of improvements have developed the former process into an industrially very useful and attractive method for the construction of aryl -aryl bonds, the need still exists for more efficient routes whereby the same outcome is accomplished, but with reduced waste and in fewer steps. In particular, the obligation to use coupling partners that are both activated is wasteful since it necessitates the installation and then subsequent disposal of stoichiometric activating agents. Furthermore, preparation of preactivated aryl substrates often requires several steps, which in itself can be a time-consuming and economically inefficient process.

3,059 citations


Journal ArticleDOI
15 Nov 2002-Angewandte Chemie
TL;DR: This review summarizes both the seminal early work and the exciting recent developments in the area of palladium-catalyzed couplings of aryl chlorides.
Abstract: Collectively, palladium-catalyzed coupling reactions represent some of the most powerful and versatile tools available to synthetic organic chemists. Their widespread popularity stems in part from the fact that they are generally tolerant to a large number of functional groups, which allows them to be employed in a wide range of applications. However, for many years a major limitation of palladium-catalyzed coupling processes has been the poor reactivity of aryl chlorides, which from the standpoints of cost and availability are more attractive substrates than the corresponding bromides, iodides, and triflates. Traditional palladium/triarylphosphane catalysts are only effective for the coupling of certain activated aryl chlorides (for example, heteroaryl chlorides and substrates that bear electron-withdrawing groups), but not for aryl chlorides in general. Since 1998, major advances have been described by a number of research groups addressing this challenge; catalysts based on bulky, electron-rich phosphanes and carbenes have proved to be particularly mild and versatile. This review summarizes both the seminal early work and the exciting recent developments in the area of palladium-catalyzed couplings of aryl chlorides.

2,297 citations


Journal ArticleDOI
17 Nov 2003-Angewandte Chemie
Abstract: The copper-mediated C(aryl)N, C(aryl)O, and C(aryl)S bond formation is an important transformation and has been developed to include a wide range of substrates. This Review highlights the recent developments in the copper-mediated (both stoichiometric and catalytic) reactions of aryl boronic acids, aryl halides, iodonium salts, siloxanes, stannanes, plumbanes, bismuthates, and trifluoroborate salts as aryl donors. In particular, the recent introduction of boronic acids as reaction partners in both O- and N-arylation has been a significant discovery and will occupy centre-stage in this review. Clear improvements can be obtained by the correct choice of copper source, base, ligands, and other additives. Mechanistic investigations should provide insight into the catalytically active species, which would aid in the development of milder, more-efficient methods.

2,221 citations



Network Information
Related Topics (5)
Cycloaddition

39.9K papers, 728.7K citations

98% related
Nucleophile

30.8K papers, 602.8K citations

98% related
Stereoselectivity

7.3K papers, 116.4K citations

98% related
Regioselectivity

22.4K papers, 465.9K citations

98% related
Electrophile

11.8K papers, 260.4K citations

98% related
Performance
Metrics
No. of papers in the topic in previous years
YearPapers
202213
20211,558
20202,032
20192,045
20182,223
20172,285

Top Attributes

Show by:

Topic's top 5 most impactful authors

Stephen L. Buchwald

320 papers, 34.2K citations

Paul Knochel

283 papers, 6.8K citations

Henri Doucet

221 papers, 5.2K citations

John F. Hartwig

204 papers, 23K citations

Xiao-Feng Wu

128 papers, 2.5K citations