The Optimization of Direct Heteroarylation and Sonogashira Cross-Coupling Reactions as Efficient and Sustainable Synthetic Methods To Access π-Conjugated Materials with Near-Infrared Absorption

2016 ◽  
Vol 4 (6) ◽  
pp. 3504-3517 ◽  
Author(s):  
Seth M. McAfee ◽  
Jonathan. R. Cann ◽  
Pierre Josse ◽  
Phillippe Blanchard ◽  
Clément Cabanetos ◽  
...  
Keyword(s):  
Infrared Absorption ◽  
Near Infrared ◽  
Cross Coupling ◽  
Synthetic Methods ◽  
Coupling Reactions ◽  
Conjugated Materials ◽  
Cross Coupling Reactions

New Synthesis of Dibenzofulvenes by Palladium-Catalyzed Double Cross-Coupling Reactions

2012 ◽  
Vol 65 (9) ◽  
pp. 1277 ◽  
Author(s):  
Masaki Shimizu ◽  
Ikuhiro Nagao ◽  
Shin-ichi Kiyomoto ◽  
Tamejiro Hiyama
Keyword(s):  
Cross Coupling ◽  
Synthetic Methods ◽  
Coupling Reactions ◽  
Cross Coupling Reactions ◽  
New Synthesis ◽  
Palladium Catalyzed ◽  
Double Cross

Palladium-catalyzed double cross-coupling reactions of 1,1-bis(pinacolato)borylalk-1-enes with 2,2′-dibromobiaryls and of 9-stannafluorenes with 1,1-dibromoalk-1-enes have been demonstrated to serve as new synthetic methods for dibenzofulvenes.

scholarly journals Polymeric Near Infrared Emitters with Bay-Annulated Indigo Moieties

2021 ◽  
Author(s):  
Ana Clara Beltran Rodrigues ◽  
Anika Eckert ◽  
João Manuel Pina ◽  
Ullrich Scherf ◽  
Joao Sergio Seixas de Melo
Keyword(s):  
Near Infrared ◽  
Cross Coupling ◽  
Building Blocks ◽  
Coupling Reactions ◽  
Cross Coupling Reactions ◽  
Infrared Emitters

Three new copolymers based on bay-annulated indigo (BAI) building blocks were synthesized through Stille-type cross-coupling reactions, alternating the electron-deficient BAI units with thiophene-based donor moieties. Those polymers showed absorption and...

Routes to some 3,6-disubstituted phthalonitriles and examples of phthalocyanines derived therefrom: An overview

2013 ◽  
Vol 17 (08n09) ◽  
pp. 649-664 ◽  
Author(s):  
Martin J. Heeney ◽  
Shaya A. Al-Raqa ◽  
Aurélien Auger ◽  
Paul M. Burnham ◽  
Andrew N. Cammidge ◽  
...  
Keyword(s):  
Metal Ion ◽  
Near Infrared ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Suzuki Coupling ◽  
Central Metal ◽  
Coupling Reactions ◽  
Negishi Coupling ◽  
Suzuki Coupling Reaction ◽  
Cross Coupling Reactions

The paper reviews a selection of synthetic pathways that provide access to 3,6-disubstituted phthalonitriles, precursors for the synthesis of 1,4,8,11,15,18,22,25-octasubstituted phthalocyanine derivatives. Early routes using Diels–Alder reactions for the synthesis of 3,6-dialkyl, 3,6-dialkoxymethyl, 3,6-dialkenyl and 3,6-diphenylphthalonitriles are appraised. However, the emphasis of the review focuses on the scope and applications of 2,3-dicyanohydroquinone as a starting material for obtaining 3,6-disubstituted phthalonitriles. The earliest example of the use of 2,3-dicyanohydroquinone concerned its O -alkylation to afford 3,6-dialkoxyphthalonitriles. These are immediate precursors to near-infrared absorbing phthalocyanine derivatives. Triflation of 2,3-dicyanohydroquinone extends the scope of the compound for phthalocyanine synthesis; the bis-triflate derivative is susceptible to S N Ar reactions and readily reacts with thiols to provide 3,6-bis(alkylsulfanyl) and 3,6-bis(arylsulfanyl)phthalonitriles. 3,6-Bis(phenylselenyl)phthalonitrile has also been obtained recently from the same precursor. Phthalocyanine derivatives obtained from them typically show a strongly bathochromically shifted Q-band absorption that is particularly sensitive to the central metal ion. The bis-triflate of 2,3-dicyanohydroquinone is also an ideal precursor for participation in cross-coupling reactions. Examples from the University of East Anglia group and elsewhere are presented which show the application of the nickel-catalyzed Negishi coupling reaction using alkylzinc halide derivatives. Yields of 3,6-dialkylphthalonitriles and 3,6-bis(substituted alkyl)phthalonitriles range from ca. 40 to 70%. Direct comparison for one example shows that the yield from the Negishi coupling method is higher than that using the Suzuki coupling protocol. Examples of the preparation of 3,6-diarylphthalonitriles from 2,3-dicyanohydroquinone bis-triflate using the Suzuki coupling reaction are reported with yields of the order of 65–70%. The review also includes a further application of 2,3-dicyanohydroquinone as a precursor to both monobromo and dibromo derivatives of 3,6-dibutoxyphthalonitrile. These compounds provide opportunities for cross-coupling at the brominated sites to provide more complex derivatives with the potential to serve as precursors of highly substituted phthalocyanine derivatives.

scholarly journals Synthesis of Conjugated Dienes in Natural Compounds

Catalysts ◽  
2022 ◽  
Vol 12 (1) ◽  
pp. 86
Author(s):  
Geoffrey Dumonteil ◽  
Sabine Berteina-Raboin
Keyword(s):  
Total Synthesis ◽  
Cross Coupling ◽  
Natural Compounds ◽  
Conjugated Dienes ◽  
Synthetic Methods ◽  
Coupling Reactions ◽  
Conjugated Diene ◽  
Cross Coupling Reactions

This review describes the various synthetic methods commonly used to obtain molecules possessing conjugated dienes. We focus on methods involving cross-coupling reactions using various metals such as nickel, palladium, ruthenium, cobalt, cobalt/zinc, manganese, zirconium, or iron, mainly through examples that aimed to access natural molecules or their analogues. Among the natural molecules covered in this review, we discuss the total synthesis of a phytohormone, Acid Abscisic (ABA), carried out by our team involving the development of a conjugated diene chain.

scholarly journals Development of Heterocycle-Substituted and Fused Azulenes in the Last Decade (2010–2020)

2020 ◽  
Vol 21 (19) ◽  
pp. 7087 ◽  
Author(s):  
Taku Shoji ◽  
Tetsuo Okujima ◽  
Shunji Ito
Keyword(s):  
Transition Metal ◽  
Physical Properties ◽  
Electrophilic Substitution ◽  
Materials Science ◽  
Cross Coupling ◽  
Synthetic Methods ◽  
Coupling Reactions ◽  
Cross Coupling Reactions ◽  
Transition Metal Catalyzed ◽  
Metal Catalyzed

Azulene derivatives with heterocyclic moieties in the molecule have been synthesized for applications in materials science by taking advantage of their unique properties. These derivatives have been prepared by various methods, involving electrophilic substitution, condensation, cyclization, and transition metal-catalyzed cross-coupling reactions. Herein, we present the development of the synthetic methods, reactivities, and physical properties for the heterocycle-substituted and heterocycle-fused azulenes reported in the last decade.

Synthesis of energy transfer cassettes via click and Suzuki–Miyaura cross coupling reactions

RSC Advances ◽  
2016 ◽  
Vol 6 (44) ◽  
pp. 37664-37671 ◽  
Author(s):  
Richa Goel ◽  
Vijay Luxami ◽  
Kamaldeep Paul
Keyword(s):  
Energy Transfer ◽  
Click Reaction ◽  
Cross Coupling ◽  
Synthetic Methods ◽  
Coupling Reactions ◽  
Cross Coupling Reactions ◽  
Palladium Catalyzed ◽  
Energy Transfer Cassettes

Novel cassettes capable of energy transfer involving simple synthetic methodsviz., click reaction at C-8 position and palladium catalyzed Suzuki–Miyaura cross coupling at C-6 position of imidazo[1,2-a]pyrazine, have been represented.

Recent Advances in the Synthesis of 2,2′-Bipyridines and Their Derivatives

Synthesis ◽  
2021 ◽  
Author(s):  
Aleksandr E. Rubtsov ◽  
Andrei V. Malkov
Keyword(s):  
Cross Coupling ◽  
Short Review ◽  
Synthetic Methods ◽  
Coupling Reactions ◽  
Substitution Pattern ◽  
Metal Free ◽  
New Methods ◽  
New Approaches ◽  
Cross Coupling Reactions ◽  
Materials Research

AbstractThe sustained interest in the synthesis of new analogues of 2,2′-bipyridines is supported by the importance of compounds featuring bipyridine core in diverse areas of chemical, biomedical and materials research, which is relayed into the development of new approaches and the expansion of existing synthetic methods. This short review covers advances in the synthesis of 2,2′-bipyridines, including both the synthesis of compounds with a given substitution pattern and the development of new methods for assembling the bipyridine core. Special attention is directed toward the use of pyridine N-oxides and metal-free protocols to facilitate the formation of bipyridines. This short review focuses primarily on reports published in the last 5–6 years.1 Introduction2 Ullmann-Type Homocoupling Reactions3 Cross-Coupling Reactions in the Synthesis of Bipyridines4 Coupling Reactions Employing Pyridine N-Oxides5 Other Methods for the Synthesis of 2,2′-Bipyridines6 Conclusions and Outlook

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