23809-98-5

Upstream product

• 1779-49-3 Methyltriphenylphosphonium bromide 
• 99-03-6 1-(3-aminophenyl)ethanone 
• 64416-49-5 3-(1-methylethenyl)nitrobenzene 
• 121-89-1 3-Nitroacetophenone 

Downstream Products

• 1295471-25-8 C₄₂H₄₉N₅O₅Si 
• 1403757-71-0 (4S,5R,6R,7S,8S,9S)-7-((tert-butyldiphenylsilyloxy)methyl)-2-(4-methoxyphenyl)-4,6-dimethyl-8-(3-(prop-1-en-2-yl)phenylamino)-3-oxa-1-azaspiro[4.4]non-1-ene-6,7,9-triol 
• 108-45-2 m-phenylenediamine 

Relevant academic research and scientific papers

Direct Electrophilic C?H Alkynylation of Unprotected 2-Vinylanilines

Unprotected aromatic amines can be used as directing groups in metal-catalyzed C?H alkynylations of alkenes. By using low amounts of an IrIIIcatalyst in combination with alkynylbenziodoxolones as electrophilic alkyne-transfer reagents, highly desirable 1,3-enynes were isolated in excellent yields of up to 98 % with Z stereoselectivity. A broad substrate scope as well as the high synthetic utility of the 1,3-enynes render this new method an efficient approach for the synthesis of five- and six-membered heterocycles. Further derivatizations of the 1,3-enynes to highly substituted quinolines through AuI- and N-bromosuccinimide-mediated exo-dig cyclizations were demonstrated.

NH2-directed C-H alkenylation of 2-vinylanilines with vinylbenziodoxolones

The first directing-group-mediated C-H alkenylation with alkenyl-λ3-iodanes as electrophilic alkene-transfer reagents has been developed. The application of free aromatic amines as challenging but synthetically valuable directing groups in combination with an IrIII catalyst enabled the synthesis of highly desirable 1, 3- dienes in excellent yields of up to 98% with high to perfect (Z, E) stereoselectivity. A broad substrate scope and further synthetic modifications are demonstrated.

Synthesis and evaluation of phenylalanine-derived trifluoromethyl ketones for peptide-based oxidation catalysis

We report the synthesis of phenylalanine-derived trifluoromethyl ketones for the in situ generation of dioxiranes for the purpose of oxidation catalysis. The key features of this synthesis include the use of a masked ketone strategy and a Negishi cross-coupling to access the parent amino acid. The derivatives can be readily incorporated into a peptide for use in oxidation chemistry and exhibit good stability and reactivity.