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Chemistry Forums for Students => Organic Chemistry Forum => Topic started by: Warren on January 07, 2021, 01:31:16 AM

Title: The reactivity of Stille coupling reagent
Post by: Warren on January 07, 2021, 01:31:16 AM
I am a Japanese university student studying organic chemistry.

Stille coupling uses organotin compounds (e.g. ArSnR3). Among them, reagents with R=Me and n-Bu are used.

What are the differences in reactivity due to steric or electronic factors?
Also, which reagent is more reactive, R=Me or n-Bu?

I hope you can answer my questions.
Title: Re: The reactivity of Stille coupling reagent
Post by: AWK on January 07, 2021, 02:36:51 AM
A good start to literature:
https://chem.libretexts.org/Bookshelves/Inorganic_Chemistry/Modules_and_Websites_(Inorganic_Chemistry)/Catalysis/Catalyst_Examples/Stille_Coupling#:~:text=The%20Stille%20coupling%20uses%20organostannane,an%2018%2Delectron%20transition%20state.
https://www2.chem.wisc.edu/areas/reich/OrgMet/tin%7B06%7D.htm
Title: Re: The reactivity of Stille coupling reagent
Post by: kriggy on January 09, 2021, 04:30:12 AM
IIRC, the trimethyltin reagents are more reactive compared to tributyltin but are also about 100 times more toxic. I was working with those once and read a review which showed numbers and the toxicity was not as high as I thought but still something to consider carefully