Regioselective Cross-Coupling Reactions of Boronic Acids with Dihalo Heterocycles

Houpis, Ioannis N.; Liu, Renmao; Wu, Yanan; Yuan, Yukuan; Wang, Youchu; Nettekoven, Ulrike

doi:10.1021/jo101223z

Cited by 30 publications

(13 citation statements)

References 22 publications

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“…[106][107][108] Using the Handy and Zhang method, many effective regioselective cross-couplings on polyhalogenated pyridines have been performed. [108][109][110][111][112][113] In continuation of the study on site-selective arylation on nicotinic acid derivatives, 114,115 additional examples of highly regioselective cross-coupling reaction of boronic acids with 2,6-dichloronicotinic acid (89) were presented by Houpis and co-workers in 2010. 109 The cross-coupling reaction with arylboronic acids having both electron-withdrawing and electron-donating substituents afforded the products in good yields and excellent selectivity (Scheme 13).…”

Section: Site-selective Synthesis Of Arylpyridinesmentioning

confidence: 99%

Arylpyridines: A Review from Selective Synthesis to Atropisomerism

Pomarański

Czarnocki²

2018

Synthesis

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Multiply arylated heterocycles are interesting structures with highly useful functions and fascinating optoelectronic and biological properties. Pyridines are an important class of compounds, playing a role in various fields of chemistry. When the pyridine ring is connected to other aromatic systems, novel stereochemical outcomes may arise. This work summarizes different methodologies applied for the synthesis of substituted arylpyridine derivatives and summarizes stereochemical phenomena resulting from atropisomerism present in certain arylated pyridines.1 Introduction2 Arylpyridines Containing meta- and para-Substituted Phenyl Groups2.1 Arylpyridine Derivatives as Amphetamine Analogues Markers2.2 Site-Selective Synthesis of Arylpyridines3 Atropisomerism in Arylpyridines Containing ortho-Substituted Phenyl Groups3.1 Synthesis of Arylpyridines Containing ortho-Substituted Phenyl Groups3.2 Other Methods for the Preparation of Arylated Pyridines4 Fully Substituted Pyridine Derivatives4.1 Site-Selective Synthesis of Fully Arylated Pyridines4.3 Atropisomerism in Densely Substituted Arylpyridines Containing ortho-Substituted Phenyl Groups5 Enantioselective Synthesis of Arylpyridine Derivatives6 Conclusion

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Section: Site-selective Synthesis Of Arylpyridinesmentioning

confidence: 99%

Arylpyridines: A Review from Selective Synthesis to Atropisomerism

Pomarański

Czarnocki²

2018

Synthesis

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“…[178] Changing the ligand and Pd sources affect the switch in chemoselectivity: the more bulky ligand directs an oxidative addition at the less hindered para position while oxidative addition is irreversible at the ortho position for a system without a similar ligand (also Class B divergence). This concept has also been successfully applied to site-selective cross-coupling of boronic acids and dichloro heterocycles such as 184 (Scheme 45 d) [179] and site-selective monoamination of dibromobenzoic acid 183 with Pd versus Cu catalysts (Scheme 45 e). [180]…”

Section: Catalytic Chemoselective Arene Functionalizationsmentioning

confidence: 99%

Catalytic Selective Synthesis

2012

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Complete control of the product of a catalytic reaction can be achieved on the basis of catalyst structure, even when the reaction conditions are nearly identical. Catalyst-controlled selectivity is well established for enantioselective catalysis but less formulated for catalytic regio-, chemo-, or product-selective reactions. This Review describes selective transformations of the same starting materials into two or more different products simply by the choice of catalyst. By collecting and highlighting examples of selective catalysis, we hope that the field will be encouraged by the progress that has been made while bringing attention to unmet needs in the design and mechanistic understanding of selective catalysts.

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“…However, the weak reactivity of C-substitution on triazole ring due to lower electronegativity in contrast with nitrogen atoms results in the few developments of C-substitution. Recently, researches have found that the metal catalyzed coupling reaction as a classical synthetic strategy can efficiently realize C-substitution on triazole ring, and much effort has been contributed to widen the application scope of C-C cross coupling reactions on aryl rings [283][284][285][286][287][288][289], especially on 1,2,4-triazole ring in organic chemistry. The reported C-substitution on 1,2,4-triazole ring is systematically involving cleavage of C-H and C-X bonds.…”

Section: C-substitution Of 124-triazole Ringmentioning

confidence: 99%

Current Developments in the Syntheses of 1,2,4-Triazole Compounds

Zhang¹,

Damu²,

Cai³

et al. 2014

COC

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Heterocyclic 1,2,4-triazole derivatives possess unusually spacious potentiality as medicinal agents, agricultural chemicals, functional materials, ionic liquids, supramolecular catalysts as well as artificial enzymes and receptors for supramolecular recognition and biomimetic catalysis, and their various researches and developments have been being a quite rapidly developing and active highlight topic with an infinite space. Numerous efforts have been directed toward various types of possible applications of 1,2,4-triazole-based compounds and a lot of important progress has been made, especially their preparations have attracted increasing attention. This review systematically summarized the recent advances in the syntheses of 1,2,4-triazole derivatives, including: (1) Cyclizations to form triazole ring; (2) Transformations of heterocyclic compounds to construct triazole ring; (3) Substitutions on 1,2,4-triazole ring; (4) Structural modifications in side chains of 1,2,4-triazole ring. It was hoped that this review would be helpful for the design and development of highly efficient preparation of 1,2,4-triazole derivatives with various sorts and varieties of extensively potential applications in medicine, agriculture, chemistry, materials, supramolecular sciences and so on.

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Regioselective Cross-Coupling Reactions of Boronic Acids with Dihalo Heterocycles

Cited by 30 publications

References 22 publications

Arylpyridines: A Review from Selective Synthesis to Atropisomerism

Arylpyridines: A Review from Selective Synthesis to Atropisomerism

Catalytic Selective Synthesis

Current Developments in the Syntheses of 1,2,4-Triazole Compounds

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