アラインを用いた遷移金属触媒反応および求電子的カップリング反応

概要

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Arynes were found to insert into carbon-tin σ-bonds of organostannanes with the aid of a palladium-iminophosphine catalyst, whereas a palladium-<I>tert</I>-alkyl isocyanide complex efficiently catalyzed the addition of cyclic disilanes (silicon-silicon σ-bonds) or distannanes (tin-tin σ-bonds). Owing to the highly electrophilic character of arynes, insertion reactions of arynes into ureas (nitrogen-carbonyl σ-bonds) or stannyl sulfides (sulfur-tin σ-bonds) took place without an added catalyst, where zwitterions arising from nucleophilic addition of the nitrogen or sulfur atom to arynes acted as key intermediates. Furthermore, arynes also accepted the nucleophilic addition of carbene moieties of isocyanides to form 1, 4-dipoles, which were convertible into iminoisobenzofuran or iminoisoindoline via the action with third components (aldehydes or <I>N</I>-tosylaldimine).
2005-06-01