Topic: How do I activate trimethyl allylsilane as a better Nucleophile (Read 4000 times)

Nitin · « **on:** December 08, 2014, 06:14:56 PM »

Hello,

How I can do this reaction in the attach file.I don't want use any Lewis acid catalyst.

Also I don't have any other substitute allyl silane.

Thanks

discodermolide · « **Reply #1 on:** December 08, 2014, 07:46:16 PM »

Try tetra-n-butylammonium fluoride. The F^- attacks the Si and initiates the nucleophillic attack.

Nitin · « **Reply #2 on:** December 10, 2014, 03:27:48 PM »

Thanks !! I had the same idea, I tried did not work. Probably I need to heat up in sealed vial. Those imino-Ene reaction probably need much higher temperature.

discodermolide · « **Reply #3 on:** December 10, 2014, 03:48:00 PM »

As far as I remember the Bu₄N⁺F^- is hydroscopic and you may need to azeotropically dry it first.

phth · « **Reply #4 on:** December 10, 2014, 04:07:40 PM »

Disco: what do you think about using a salt like KFHF instead? because it may be easier to dry (MP 239C) and it is more nucleophilic than F-

discodermolide · « **Reply #5 on:** December 10, 2014, 08:58:46 PM »

You could try that. I was going to suggest HF in acetonitrile but thought that may be too acidic for your system.

clarkstill · « **Reply #6 on:** December 11, 2014, 01:13:00 PM »

I think TBAT is a good anhydrous alternative to TBAF:

http://www.sigmaaldrich.com/catalog/product/aldrich/441457?lang=en&region=GB

Topic: How do I activate trimethyl allylsilane as a better Nucleophile (Read 4000 times)

Nitin

How do I activate trimethyl allylsilane as a better Nucleophile

discodermolide

Re: How do I activate trimethyl allylsilane as a better Nucleophile

Nitin

Re: How do I activate trimethyl allylsilane as a better Nucleophile

discodermolide

Re: How do I activate trimethyl allylsilane as a better Nucleophile

phth

Re: How do I activate trimethyl allylsilane as a better Nucleophile

discodermolide

Re: How do I activate trimethyl allylsilane as a better Nucleophile

clarkstill

Re: How do I activate trimethyl allylsilane as a better Nucleophile

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