August 14, 2020, 10:47:29 PM
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Topic: Cross coupling w/ epoxide  (Read 301 times)

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Offline phth

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Cross coupling w/ epoxide
« on: June 11, 2020, 12:08:30 AM »
Is it possible to perform a cross-coupling reaction in the presence of an epoxide?

Offline rolnor

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Re: Cross coupling w/ epoxide
« Reply #1 on: June 11, 2020, 03:46:01 AM »
What do you think? Is it Suzuki, Stille or what?

Offline phth

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Re: Cross coupling w/ epoxide
« Reply #2 on: June 11, 2020, 02:16:24 PM »
It seems like they are reactive for reasons other than competing oxidative insertion with palladium, for example. I found one example with Suzuki conditions in hot benzene. I was wondering if there are milder alternatives.

Offline rolnor

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Re: Cross coupling w/ epoxide
« Reply #3 on: June 11, 2020, 04:29:56 PM »
I have made some reactions with epoxides, generally they are less reactive than for example iodides. If you want to react a epoxide with diethyl malonate under basic conditions you need many hours and heat. You can open epoxides with dialkyllithiocuprates if you use BF3Et2O to activate the epoxide. The question is what coupling you want to do, is it a arylboronic acid and a aryliodide for example I think this would work, I dont se why the epoxide should open.

Offline phth

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Re: Cross coupling w/ epoxide
« Reply #4 on: June 11, 2020, 05:15:42 PM »
Thanks, Diene synthesis in the presence of an epoxide: breaking the diene into two alkenes as a key disconnection.

Offline rolnor

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Re: Cross coupling w/ epoxide
« Reply #5 on: June 12, 2020, 04:43:06 AM »
Is this Diels-Alder?

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