Expedited Development through Parallel Reaction Screening: Application to PTC-Mediated Knoevenagel Condensation

Autor:	John Corona, Roman Davis, Sandeep B. Kedia, Mark B. Mitchell
Rok vydání:	2010
Předmět:	chemistry.chemical_classification Reaction mechanism Organic Chemistry Aldehyde Tautomer law.invention Elimination reaction chemistry Aldol reaction law Organic chemistry Knoevenagel condensation Physical and Theoretical Chemistry Crystallization Microreactor
Zdroj:	Organic Process Research & Development. 14:712-715
ISSN:	1520-586X 1083-6160
DOI:	10.1021/op100026u
Popis:	Parallel microreactor screening enabled rapid identification of effective conditions for PTC-mediated Knoevenagel condensation between aldehyde (1) and thiazalone (2), affording a dramatic reduction in cycle time when compared to traditional conditions. Interesting facets of the reaction mechanism were revealed from kinetic profiling, specifically the operation of an extractive PTC mechanism with a pH optimum for the Knoevenagel condensation, a pKa optimum for the elimination reaction and the requirement for crystallization of aldol tautomer (4) to drive the reaction to completion.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::e6ba0e7a16fb2ad17aafca1913365d30 https://doi.org/10.1021/op100026u Zobrazit plný text záznamu