Name: stille coupling overview: organostannanes with halides
Uploaded: 2023-01-10T17:30:47
Description: Stille coupling reaction, named after its pioneer John K. Stille, involves the coupling of an organic electrophile with an organostannane compound in the ...

stille coupling overview: organostannanes with halides

Stille coupling reaction, named after its pioneer John K. Stille, involves the coupling of an organic electrophile with an organostannane compound in the presence of an active Pd(0) species to form a coupled product comprising both coupling partners.
<img alt="Figure1" src="/files/ftp_upload/12309/12309_PT_Figure_1.svg" style="text-align: center; height: 34px;" />
The organic electrophiles are aryl, or vinyl halides (I, Br, Cl), or triflates (OTf). The nucleophilic partners are organostannane compounds comprising the metal at the center, bonded to three identical alkyl (tributyl- or trimethyl-) groups and one distinct coupling partner&#8212;an aryl, vinyl, or a benzyl group. Most organostannane compounds are commercially available; however, they can also be readily synthesized by reacting tributyl chloride with Grignard reagents.
<img alt="Figure2" src="/files/ftp_upload/12309/12309_PT_Figure_2.svg" style="text-align: center; height: 22px;" />
Stille coupling can be used to join two aromatic systems to generate biaryl systems.
<img alt="Figure3" src="/files/ftp_upload/12309/12309_PT_Figure_3.svg" style="text-align: center; height: 43px;" />
Similarly, using aryl and vinyl coupling partners, styrene derivatives can be generated.
<img alt="Figure4" src="/files/ftp_upload/12309/12309_PT_Figure_4.svg" style="text-align: center; height: 45px;" />
Stille coupling is also used to prepare conjugated dienes. The reactions are observed to be stereospecific with retention of configuration at each C&#8211;C double bond.
<img alt="Figure5" src="/files/ftp_upload/12309/12309_PT_Figure_5.svg" style="text-align: center; height: 60px;" />
Coupling an aryl with a benzyl group forms a new bond with sp2- and sp3- carbon centers.
<img alt="Figure6" src="/files/ftp_upload/12309/12309_PT_Figure_6.svg" style="text-align: center; height: 75px;" />
Further, some of the applications of Stille coupling are observed towards the synthesis of aldehydes and ketones.
<img alt="Figure7" src="/files/ftp_upload/12309/12309_PT_Figure_7.svg" style="text-align: center; height: 75px;" />

Stille Coupling Overview: Organostannanes with Halides

Stille coupling reaction, named after its pioneer John K. Stille, involves the coupling of an organic electrophile with an organostannane compound in the ...