Recent Advances in the Substitution Reactions of Triorganylstannyl Ions with Aromatic Compounds by the SRN1 Mechanism. Synthetic Applications 英文参考文献.docVIP

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Recent Advances in the Substitution Reactions of Triorganylstannyl Ions with Aromatic Compounds by the SRN1 Mechanism. Synthetic Applications 英文参考文献.doc

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Recent Advances in the Substitution Reactions of Triorganylstannyl Ions with Aromatic Compounds by the SRN1 Mechanism. Synthetic Applications 英文参考文献

Molecules 2000, 5, 1068-1079 molecules ISSN 1420-3049 ? 2000 by MDPI Review Recent Advances in the Substitution Reactions of Triorganylstannyl Ions with Aromatic Compounds by the SRN1 Mechanism. Synthetic Applications Eduardo F. Córsico, Al Postigo and Roberto A. Rossi* INFIQC, Departamento de Química Orgánica, Facultad de Ciencias Químicas, Universidad Nacional de Córdoba. Ciudad Universitaria, 5000 Córdoba, Argentina Tel.: (54) (351) 433-4170, Fax: (54) (351) 433-3030, E-mail: rossi@.ar Received: 30May2000;revisedform18August2000/ Accepted: 5September2000/ Published: 11September 2000 Abstract: A review on the reactions of triorganyl stannyl ions with haloarenes is presented. Emphasis on the synthetic applications of the resulting triorganyl stannyl aryl compounds is made, with their inherent potential to build large molecules through the SRN1 sequence, i.e. ArX?ArSnR3?ArAr, which can be iteratively repeated when appropriately substituted substrates are chosen. Keywords: stannyl anions, SRN1, Stille reactions. Introduction The reaction of triorganostannyl ions as nucleophiles with haloarenes has long been known, and the prod- ucts obtained depend on the nucleophile, solvent, and on the reaction conditions. Thus, the reactions of so- dium trimethyltin (NaSnMe3) with halobenzenes (chloro-, bromo- and iodo-) in tetraglyme as solvent afford phenyltrimethyltin (Me3SnPh) and variable amounts of reduction product benzene along with diphenyldimeth- yltin (Ph2SnMe2) and tetramethyltin (SnMe4). From trapping experiments and solvent effects it has been pro- posed that the reaction occurs by a halogen metal exchange (HME) mechanism in a solvent cage. The forma- tion of secondary products, Ph2SnMe2 and SnMe4, has been ascribed to the decomposition of NaSnMe3 into NaMe and dimethylstannylene [1]. The reaction of o-dibromobenzene with NaSnMe3 affords the disubstitu- tion product o-bis(trimethylstannyl) benzene