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Topic: What is your most important organic reaction in your professional life  (Read 689 times)

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Offline kamiyu2550

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In your professional life (e.g. PhD or professional workers), which organic reaction is most important to you?

Offline rolnor

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Re: What is your most important organic reaction in your professional life
« Reply #1 on: September 28, 2019, 03:47:57 AM »
It depends on the project, not possible to generalize.

Offline Babcock_Hall

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Re: What is your most important organic reaction in your professional life
« Reply #2 on: September 30, 2019, 10:52:10 AM »
Substitutions involving the trifluoromethanesulfonyl group leaving have helped me twice at different points in my career.

Offline kamiyu2550

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Re: What is your most important organic reaction in your professional life
« Reply #3 on: September 30, 2019, 11:28:24 AM »
Substitutions involving the trifluoromethanesulfonyl group leaving have helped me twice at different points in my career.

I guess what you did is using triflate as pseduo-halide in cross-coupling reaction, right?

For simple SN2 reaction people may use OTs group as it is way cheaper.

Triflate reactivity in between iodine and bromine.

Offline Babcock_Hall

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Re: What is your most important organic reaction in your professional life
« Reply #4 on: September 30, 2019, 04:08:25 PM »
I used trimethylsilyl trifluoromethanesulfonate and tetrabutylammonium iodide in place of TMSI.  I was trying to remove the methyl ester groups from a very labile phosphate ester.  TMSI is not the easiest compound with which to work.

Offline kamiyu2550

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Re: What is your most important organic reaction in your professional life
« Reply #5 on: September 30, 2019, 06:54:46 PM »
I used trimethylsilyl trifluoromethanesulfonate and tetrabutylammonium iodide in place of TMSI.  I was trying to remove the methyl ester groups from a very labile phosphate ester.  TMSI is not the easiest compound with which to work.

Ok, I see. Please confirm my logic here:

TMSI is very reactive and hard to handle and you wanna make it in situ. TMSI in this case serves as a very mild deprotecting agent. For your methyl phosphate ester, the reaction with TMSI will give TMS phosphate and methyl iodide.

Is this correct?

Offline Babcock_Hall

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Re: What is your most important organic reaction in your professional life
« Reply #6 on: September 30, 2019, 07:45:35 PM »
Yes; if memory serves me, we ran the reaction at -30 °C in DCM.  Once you have a trimethylsilyl phosphate ester, that sort of compound is very easily solvolyzed in alcohols or in water, sometimes in the presence of a weak base.

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