[Serenagreene]

I know that what I have attached is probably totally wrong.  Should never had missed class .  So if someone can point me in the right direction - nice explanation on a web site would be great or even if this reaction has a proper name.... 

Thanks,

-Serena

P.S.  In case no one has mentioned it you all are wonderful!!! 

[azmanam]

I think this is what you're looking for

http://www.as.ysu.edu/~pnorris/Semesters/6942S2008/Chapter7.pdf

[ARGOS++]

Dear Serenagreene;

I see it also as a small Variant of the:   "Suzuki Coupling”.


Good Luck!
                    ARGOS⁺⁺

[Serenagreene]

Thanks for the link and the name of the reaction.  Now I'm trying a Heck reaction and the first step is to make the triflate.  I'm thinking the below is how I would do the reaction.  I was given the first molecule and the last molecule is my target.  Can someone take a quick look at this and tell me if it's okay?

-Serena

[azmanam]

Triflic acid is no good.  What do you propose to be the mechanism of that first step, and what triflate source do you think might be better?

Other than that, I think you're fine.

[Serenagreene]

Looking at it again I think I need to use a Lewis acid instead of a base, perhaps LiAlH₄ in water. This would give me the alcohol.  Then could I add trifluoromethanesulfonyl bromide with LDA in DMF?

I actually am not sure what triflates are out there.  I don't suppose there is a nice link to a page about how to prepare triflates. I can't seem to find one in the books we are using (Advanced Organic Chemistry, Part B: Reactions and Synthesis by Carey & Sundberg and Organic Chemistry an intermediate text by Hoffman). 

-Serena

[azmanam]

Reducing first is no good either   Look at your alcohol to triflate step and see if you notice the major difference.

I think you can attach the triflate straight out from the pyridinone.  Maybe try some tautomerization operations to look at another form of the pyridinone.  I think if you combine your pyridinone with that triflic bromide you have if your second attempt, you may be starting to get on the right track.  You'll need another reagent in that step, but you're getting there.

[Serenagreene]

I'll take another stab at it after I get out of Calculus.

-Serena

[agrobert]

Triflic anhydride is a better electrophile than the bromide.

Triflates are generally used in coupling reactions because they are good leaving groups (oxidative-addition).

[Serenagreene]

Okay I think this should work.  I read that vinyl triflates formed from ketone are done through the enolate with the use of N-phenyltriflamide. 

Thanks,

-Serena