Single-step synthesis of styryl phosphonic acids via palladium-catalyzed Heck coupling of vinyl phosphonic acid with aryl halides

2017 ◽  
Vol 53 (92) ◽  
pp. 12454-12456 ◽  
Author(s):  
Brett W. McNichols ◽  
Joshua T. Koubek ◽  
Alan Sellinger
Keyword(s):  
Phosphonic Acid ◽  
Single Step ◽  
Aryl Halides ◽  
Heck Coupling ◽  
Phosphonic Acids ◽  
Palladium Catalyzed

We have developed a single step palladium-catalyzed Heck coupling of aryl halides with vinyl phosphonic acid to produce functionalized (E)-styryl phosphonic acids.

Synthesis of partially and fully fused polyaromatics by annulative chlorophenylene dimerization

Science ◽  
2018 ◽  
Vol 359 (6374) ◽  
pp. 435-439 ◽  
Author(s):  
Yoshito Koga ◽  
Takeshi Kaneda ◽  
Yutaro Saito ◽  
Kei Murakami ◽  
Kenichiro Itami
Keyword(s):  
Bond Activation ◽  
Graphene Nanoribbons ◽  
Single Point ◽  
Single Step ◽  
Aryl Halides ◽  
Powerful Method ◽  
Carbon Hydrogen Bond Activation ◽  
Palladium Catalyzed ◽  
Aromatic Systems ◽  
Functionally Diverse

Since the discovery by Ullmann and Bielecki in 1901, reductive dimerization (or homocoupling) of aryl halides has been extensively exploited for the generation of a range of biaryl-based functional molecules. In contrast to the single-point connection in these products, edge-sharing fused aromatic systems have not generally been accessible from simple aryl halides via annulation cascades. Here we report a single-step synthesis of fused aromatics with a triphenylene core by the palladium-catalyzed annulative dimerization of structurally and functionally diverse chlorophenylenes through double carbon-hydrogen bond activation. The partially fused polyaromatics can be transformed into fully fused, small graphene nanoribbons, which are otherwise difficult to synthesize. This simple, yet powerful, method allows access to functional π-systems of interest in optoelectronics research.

scholarly journals A Sustainable Improvement of ω-Bromoalkylphosphonates Synthesis to Access Novel KuQuinones

Organics ◽  
2021 ◽  
Vol 2 (2) ◽  
pp. 107-117
Author(s):  
Mattia Forchetta ◽  
Valeria Conte ◽  
Giulia Fiorani ◽  
Pierluca Galloni ◽  
Federica Sabuzi
Keyword(s):  
Metal Oxides ◽  
Phosphonic Acid ◽  
Organic Molecules ◽  
Building Blocks ◽  
Reaction Conditions ◽  
Phosphonic Acids ◽  
Sustainable Improvement ◽  
Phosphonate Esters ◽  
First Time ◽  
Complex Organic

Owing to the attractiveness of organic phosphonic acids and esters in the pharmacological field and in the functionalization of conductive metal-oxides, the research of effective synthetic protocols is pivotal. Among the others, ω-bromoalkylphosphonates are gaining particular attention because they are useful building blocks for the tailored functionalization of complex organic molecules. Hence, in this work, the optimization of Michaelis–Arbuzov reaction conditions for ω-bromoalkylphosphonates has been performed, to improve process sustainability while maintaining good yields. Synthesized ω-bromoalkylphosphonates have been successfully adopted for the synthesis of new KuQuinone phosphonate esters and, by hydrolysis, phosphonic acid KuQuinone derivatives have been obtained for the first time. Considering the high affinity with metal-oxides, KuQuinones bearing phosphonic acid terminal groups are promising candidates for biomedical and photo(electro)chemical applications.

Palladium Catalyzed Cascade Azidation/Carbonylation of Aryl Halides with Sodium Azide for the Synthesis of Amides

2021 ◽  
Author(s):  
Zhuang Qi ◽  
Shan‐Shan Li ◽  
Lin Li ◽  
Qi Qin ◽  
Li‐Miao Yang ◽  
...  
Keyword(s):  
Sodium Azide ◽  
Aryl Halides ◽  
Palladium Catalyzed

Palladium-Catalyzed Olefinations of Aryl Halides (Heck Reaction) and Related Transformations

ChemInform ◽  
2005 ◽  
Vol 36 (44) ◽  
Author(s):  
Matthias Beller ◽  
Alexander Zapf ◽  
Thomas H. Riermeier
Keyword(s):  
Heck Reaction ◽  
Aryl Halides ◽  
Palladium Catalyzed

ChemInform Abstract: A General and Efficient Catalyst for Palladium-Catalyzed C-O Coupling Reactions of Aryl Halides with Primary Alcohols.

ChemInform ◽  
2010 ◽  
Vol 42 (4) ◽  
pp. no-no
Author(s):  
Saravanan Gowrisankar ◽  
Alexey G. Sergeev ◽  
Pazhamalai Anbarasan ◽  
Anke Spannenberg ◽  
Helfried Neumann ◽  
...  
Keyword(s):  
Aryl Halides ◽  
Coupling Reactions ◽  
Primary Alcohols ◽  
Efficient Catalyst ◽  
Palladium Catalyzed
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