Stille protocol

The Stille protocol is now well established, and finds many uses in preparative chemistry. Especially, application to the synthesis of bioactive substances and functional materials is noteworthy. The choice of catalyst and solvent, however, is still remained veiled. If the reaction to be attempted is not well documented, one should first try to find the most suitable reaction conditions. Organotin compounds can be extremely toxic, and tributyltin compounds are recently suspected to be endocrine disrupters. The presence of even traces of organotin contaminants in organic products must be avoided, as far as possible. In spite of these problems, the Stille protocol will continue to be a favorite method for car-bon-carbon-bond formation, owing to the mildness of the reaction conditions and the functional tolerability of both substrates and reagents. 

Kosugi, M., Fugami, K. Overview of the Stille protocol with Sn. Handbook of Organopalladium Chemistry for Organic Synthesis 2002,1,... 

Other efforts in the mechanistic study of the Kosugi-Stille protocol have been geared toward directly observing and/or... 

The Stille protocol is now well established and finds many uses in preparative chemistry. Especially noteworthy is application to the synthesis of bioactive substances. The choice... 

AUcynylstannanes can cross-couple with a variety of other functional groups employing the Stille protocol. Couphng to acyl chlorides is a well-known procedure that affords aUcynylketones in respectable yields. Other reports include alkynyltin cross-couplings with a-haloethers and a-halocarbonyls, enol phosphinates and phosphonates, alkenyl(phenyl)iodonium salts, alkynyl halides, and allyl hahdes (Table 9.18). Alkynylstannanes have also been shown to cross-couple with iron halides under the Stille conditions to effectively form iron-carbon bonds. 

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