A concise synthesis of biaryl PDE4D allosteric modulators

Dalby, Amy L.; Mo, Xuesheng; Stoa, Robert; Wroblewski, Nathaniel; Zhang, Zheng; Hagen, Timothy J.

doi:10.1016/j.tetlet.2013.03.063

Cited by 5 publications

(1 citation statement)

References 13 publications

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“…The synthesis of complicated systems with different functional groups is often associated with the creation of C-C bonds by cross-coupling reactions with the use of transition-metal catalysis and this type of reaction remains one of the most important tools in organic or organometallic chemistry. [1][2][3][4][5][6][7][8][9][10][11][12][13][14][15][16][17][18][19][20] Transition-metal catalysis allows the formation of different types of C-C bonds, including the bond between two trigonal carbon atoms which is rather difficult to perform by classical methods. The importance and usefulness of modern methods was recently rewarded by the award of the 2010 Nobel Prize in Chemistry to R. Heck, E. Negishi, and A. Suzuki for the development of palladiumcatalyzed cross-coupling reactions, especially useful for the synthesis of biaryls, including those exhibiting axial chirality.…”

Section: Introductionmentioning

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: Introductionmentioning

confidence: 99%

Arylpyridines: A Review from Selective Synthesis to Atropisomerism

Pomarański

Czarnocki²

2018

Synthesis

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Biaryls

2018

Privileged Structures in Drug Discovery

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Abnormal NHC Palladium(II) Complex Containing CNN Pincer Skeleton and Its Application to Suzuki‐Miyaura Coupling of Aryl Chlorides in Water

et al. 2023

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The excellent catalytic activities of abnormal NHC carbene complexes, where the C2 position remains unaffected, and coordination occurs at the C4 or C5 position of the imidazolium ring, is still a fascinating but scarce area of research. This present work reports a palladium complex (LPdBr) bearing abnormal NHC with CNN pincer architecture. It is synthesized from imidazolium‐based quinoline ligand (LH) with Pd(OAc)2 via ‐NH and carbene deprotonation. The complex was fully characterized by NMR spectroscopy (1D and 2D) and high‐resolution mass spectrometry (HRMS). The structure and abnormal coordination modes of the complex are further confirmed with the help of single‐crystal X‐ray diffraction. The studies revealed the abnormal coordination mode in LPdBr where C5 carbon of the imidazolium ring participates in bonding, leaving the C2 position unaffected. The catalytic potential of complex LPdBr was investigated in the Pd‐catalyzed Suzuki‐Miyaura coupling of various aryl/heteroaryl chlorides with different aryl/naphthyl/phenanthryl boronic acids. The catalyst LPdBr successfully activated various less‐activated aryl chloride substrates. LPdBr also exhibited good catalytic activity at 1 mol% Pd loading under microwave irradiation and in green solvent water. The mechanism of the catalytic cycle is investigated and proposed by HRMS.

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A concise synthesis of biaryl PDE4D allosteric modulators

Cited by 5 publications

References 13 publications

Arylpyridines: A Review from Selective Synthesis to Atropisomerism

Arylpyridines: A Review from Selective Synthesis to Atropisomerism

Biaryls

Abnormal NHC Palladium(II) Complex Containing CNN Pincer Skeleton and Its Application to Suzuki‐Miyaura Coupling of Aryl Chlorides in Water

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