Selective Synthetic Routes to Sterically Hindered Unsymmetrical Diaryl Ketones via Arylstannanes

Bulky arylstannanes and bulky aroyl chlorides are good reaction partners for the synthesis of two-, three-, and even four-ortho-substituted benzophenones, in good to excellent isolated yields (47−91%). Three simple and direct routes, with differential advantages, are proposed: (i) a catalyst-free pr...

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Bibliographic Details
Published in:Journal of organic chemistry 2011-03, Vol.76 (6), p.1707-1714
Main Authors: Lo Fiego, Marcos J, Silbestri, Gustavo F, Chopa, Alicia B, Lockhart, María T
Format: Article
Language:English
Subjects:
Catalysis
Chemistry
Chlorobenzenes - chemistry
Exact sciences and technology
Indicators and Reagents - chemistry
Indium - chemistry
Ketones - chemical synthesis
Ketones - chemistry
Kinetics and mechanisms
Noncondensed benzenic compounds
Organic chemistry
Preparations and properties
Reactivity and mechanisms
Substrate Specificity
Tin Compounds - chemistry
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Summary:Bulky arylstannanes and bulky aroyl chlorides are good reaction partners for the synthesis of two-, three-, and even four-ortho-substituted benzophenones, in good to excellent isolated yields (47−91%). Three simple and direct routes, with differential advantages, are proposed: (i) a catalyst-free protocol, in o-dichlorobenzene (ODCB) at 180 °C; (ii) a room temperature protocol, using AlCl3 (0.5 equiv), in dichloromethane (DCM); and (iii) a solvent-free, indium-promoted procedure. A radical mechanism is proposed for the indium-mediated reactions.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo102366q