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Transition-metal-free formal Sonogashira coupling and alpha-carbonyl arylation reactions.
- Source :
-
Chemistry (Weinheim an der Bergstrasse, Germany) [Chemistry] 2010 Mar 22; Vol. 16 (12), pp. 3783-90. - Publication Year :
- 2010
-
Abstract
- Transition-metal-free formal Sonogashira coupling and alpha-carbonyl arylation reactions have been developed. These transformations are based on the nucleophilic aromatic substitution (S(N)Ar) of beta-carbonyl sulfones to electron-deficient aryl fluorides, producing a key intermediate that, depending on the reaction conditions, gives the aromatic alkynes or alpha-aryl carbonyl compounds. The development of these reactions is presented and, based on investigations under basic and acidic conditions, mechanisms have been proposed. To develop the formal Sonogashira coupling further, a milder, two-step protocol is also disclosed that expands the reaction concept. The scope of these reactions is demonstrated for the synthesis of Sonogashira and alpha-carbonyl arylated products from a range of electron-deficient aryl fluorides with a variety of functional groups and aryl-, heteroaryl-, alkyl-, and alkoxy-substituted sulfone nucleophiles. These transition-metal-free reactions complement the metal-catalyzed versions in terms of substitution patterns, simplicity, and reaction conditions.
Details
- Language :
- English
- ISSN :
- 1521-3765
- Volume :
- 16
- Issue :
- 12
- Database :
- MEDLINE
- Journal :
- Chemistry (Weinheim an der Bergstrasse, Germany)
- Publication Type :
- Academic Journal
- Accession number :
- 20175160
- Full Text :
- https://doi.org/10.1002/chem.200902911