Meta- and Para-Difunctionalization of Arenes via an Ortho-Magnesiation and a Subsequent Sulfoxide-Magnesium Exchange

Autor:	Paul Knochel, Laurin Melzig, Christian B. Rauhut
Rok vydání:	2009
Předmět:	Quenching (fluorescence) Magnesium Metalation Aryl Organic Chemistry chemistry.chemical_element Sulfoxide Medicinal chemistry Catalysis chemistry.chemical_compound chemistry Reagent Electrophile Moiety
Zdroj:	Synthesis. 2009:1041-1048
ISSN:	1437-210X 0039-7881
DOI:	10.1055/s-0028-1087984
Popis:	Highly functionalized 1,2,4-trisubstituted arenes can be prepared on large scale by a two-step sequence, triggered by an aryl sulfoxide group. In the first step, the sulfoxide moiety acts as a metalation directing group, allowing a smooth magnesiation with tmp-MgCl-LiCl. After a quenching reaction with an electrophile, the resulting sulfoxide is converted with i-PrMgCl·LiCl into a second magnesium reagent (sulfoxide-magnesium exchange), which can be trapped with various electrophiles. The highly chemoselective tmpMgCl·LiCl and i-PrMgCl·LiCl are compatible with a broad range of functional groups (FG = F, Cl, CF 3 , CN, CO 2 t-Bu, alkynyl).
Databáze:	OpenAIRE
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