27111-45-1Relevant articles and documents
Palladium-Catalyzed Chlorocarbonylation of Aryl (Pseudo)Halides Through In Situ Generation of Carbon Monoxide
Bismuto, Alessandro,Boehm, Philip,Morandi, Bill,Roediger, Sven
supporting information, p. 17887 - 17896 (2020/08/19)
An efficient palladium-catalyzed chlorocarbonylation of aryl (pseudo)halides that gives access to a wide range of carboxylic acid derivatives has been developed. The use of butyryl chloride as a combined CO and Cl source eludes the need for toxic, gaseous carbon monoxide, thus facilitating the synthesis of high-value products from readily available aryl (pseudo)halides. The combination of palladium(0), Xantphos, and an amine base is essential to promote this broadly applicable catalytic reaction. Overall, this reaction provides access to a great variety of carbonyl-containing products through in situ transformation of the generated aroyl chloride. Combined experimental and computational studies support a reaction mechanism involving in situ generation of CO.
Metathesis-active ligands enable a catalytic functional group metathesis between aroyl chlorides and aryl iodides
Lee, Yong Ho,Morandi, Bill
, p. 1016 - 1022 (2018/09/06)
Current methods for functional group interconversion have, for the most part, relied on relatively strong driving forces which often require highly reactive reagents to generate irreversibly a desired product in high yield and selectivity. These approaches generally prevent the use of the same catalytic strategy to perform the reverse reaction. Here we describe a catalytic functional group metathesis approach to interconvert, under CO-free conditions, two synthetically important classes of electrophiles that are often employed in the preparation of pharmaceuticals and agrochemicals—aroyl chlorides (ArCOCl) and aryl iodides (ArI). Our reaction design relies on the implementation of a key reversible ligand C–P bond cleavage event, which enables a non-innocent, metathesis-active phosphine ligand to mediate a rapid aryl group transfer between the two different electrophiles. Beyond enabling a practical and safer approach to the interconversion of ArCOCl and ArI, this type of ligand non-innocence provides a blueprint for the development of a broad range of functional group metathesis reactions employing synthetically relevant aryl electrophiles.
Functional Group Transposition: A Palladium-Catalyzed Metathesis of Ar-X σ-Bonds and Acid Chloride Synthesis
De La Higuera Macias, Maximiliano,Arndtsen, Bruce A.
supporting information, p. 10140 - 10144 (2018/08/23)
We describe the development of a new method to use palladium catalysis to form functionalized aromatics: via the metathesis of covalent σ-bonds between Ar-X fragments. This transformation demonstrates the dynamic nature of palladium-based oxidative addition/reductive elimination and offers a straightforward approach to incorporate reactive functional groups into aryl halides through exchange reactions. The reaction has been exploited to assemble acid chlorides without the use of high energy halogenating or toxic reagents and, instead, via the metathesis of aryl iodides with other acid chlorides.
New photoactivatable analogues of glutathione disulfide
Bernardi, Dan,Dicko, Amadou,Kirsch, Gilbert
, p. 509 - 513 (2007/10/03)
New photoactivatable analogues of glutathione disulfide (GSSG) bearing new benzophenone-like photophores were synthesized by using an improved coupling reaction. Georg Thieme Verlag Stuttgart.
An efficient synthesis of diaryl ketones by iron-catalyzed arylation of aroyl cyanides
Duplais, Christophe,Bures, Filip,Sapountzis, Ioannis,Korn, Tobias J.,Cahiez, Gerard,Knochel, Paul
, p. 2968 - 2970 (2007/10/03)
An alternative to acyl chlorides: Iron(III)-catalyzed arylation of aroyl and heteroaroyl cyanides with aryl magnesium reagents (see example in scheme) provides an easy and mild approach to polyfunctionalized diaryl ketones in yields up to 98%.
Nonsteroidal estrogens bearing acyl azide functions: potential electrophilic and photoaffinity labeling agents for the estrogen receptor
Pinney, Kevin G,.,Carlson, Kathryn E.,Katzenellenbogen, John A.
, p. 222 - 232 (2007/10/02)
In an effort to develop novel affinity labeling agents for the estrogen receptor, we have synthesized two nonsteroidal ligands, a 1-aroyl-2-aryl tetralin system (1) and a 2-aryl-3-aroylbenzothiophene system (2).These agents, patterned after the Lilly a
N-(Benzimidazol-2-yl)arylcarboxamides as ultraviolet (UV) light absorbers
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, (2008/06/13)
This invention relates to compositions containing N-(benzimidazol-2-yl)arylcarboxamides as ultraviolet (UV) light absorbers. The compounds are useful to protect UV sensitive materials, particularly plastic compositions, or ingredients thereof such as dyes, anti-microbial agents, or plasticizers from attack by ultraviolet light. The compositions are suitable for those uses where UV protection is required only for short periods of time, for example in sun tan lotions, as well as for uses which require protection for extended periods of time.
