70837-47-7Relevant academic research and scientific papers
Halogen Bond-Catalyzed Friedel-Crafts Reactions of Aldehydes and Ketones Using a Bidentate Halogen Bond Donor Catalyst: Synthesis of Symmetrical Bis(indolyl)methanes
Liu, Xuelei,Ma, Shuang,Toy, Patrick H.
supporting information, p. 9212 - 9216 (2019/11/14)
The use of a halogen bond donor to catalyze Friedel-Crafts reactions of indoles with a range of aldehydes and ketones to directly produce bis(indolyl)methanes, including the natural products arsindoline A, arundine, trisindoline, and vibrindole A, is reported. The bidentate catalyst used in these reactions proved to be more effective than a monondentate analogue, a thiourea commonly used as an organocatalyst, and even a trityl cation that has been used previously in the synthesis of bis(indolyl)methanes.
A biomolecule-compatible visible-light-induced azide reduction from a DNA-encoded reaction-discovery system
Chen, Yiyun,Kamlet, Adam S.,Steinman, Jonathan B.,Liu, David R.
scheme or table, p. 146 - 153 (2012/02/17)
Using a system that accelerates the serendipitous discovery of new reactions by evaluating hundreds of DNA-encoded substrate combinations in a single experiment, we explored a broad range of reaction conditions for new bond-forming reactions. We discovered reactivity that led to a biomolecule-compatible, Ru(II)-catalysed azide-reduction reaction induced by visible light. In contrast to current azide-reduction methods, this reaction is highly chemoselective and is compatible with alcohols, phenols, acids, alkenes, alkynes, aldehydes, alkyl halides, alkyl mesylates and disulfides. The remarkable functional group compatibility and mild conditions of the reaction enabled the azide reduction of nucleic acid and oligosaccharide substrates, with no detectable occurrence of side reactions. The reaction was also performed in the presence of a protein enzyme without the loss of enzymatic activity, in contrast to two commonly used azide-reduction methods. The visible-light dependence of this reaction provides a means of photouncaging functional groups, such as amines and carboxylates, on biological macromolecules without using ultraviolet irradiation.
Trityl chloride as a novel and efficient organic catalyst for room temperature preparation of bis(indolyl)methanes under solvent-free conditions in neutral media
Khalafi-Nezhad,Parhami,Zare,Moosavi Zare,Hasaninejad,Panahi
, p. 617 - 621 (2008/12/21)
A simple, clean, and highly efficient solvent-free procedure for the preparation of bis(1H-indol-3-yl)methanes is described from the reaction of carbonyl compounds (aldehydes and ketones) with 1H-indole in the presence of trityl chloride as a catalyst. Th
