Topic: Phenyl acetylene (Read 1252 times)

harmonic_op · « **on:** May 30, 2019, 09:06:48 AM »

Hello everyone,

Is it possible to synthesize Phenylacetylene using iodobenzene using the coupling reactions?
If yes then can someone help me out with the scheme?

rolnor · « **Reply #1 on:** May 30, 2019, 10:22:18 AM »

Can you suggest a coupling reaction? Acetylene has twoo reactive ends, how will you avoid forming diphenyl acetylene?

harmonic_op · « **Reply #2 on:** May 30, 2019, 03:02:31 PM »

Quote from: rolnor on May 30, 2019, 10:22:18 AM

Can you suggest a coupling reaction? Acetylene has twoo reactive ends, how will you avoid forming diphenyl acetylene?

Is it possible using sonogashira coupling where our desire product is phenylacetylene only.?

clarkstill · « **Reply #3 on:** May 30, 2019, 03:46:38 PM »

I think the old trick is to use TMS-acetylene for the Sonogashira, then cleave the TMS with K2CO3/MeOH. I guess you could also use a large excess of acetylene to favour mono-addition, but handling gases is a pain tbh.

wildfyr · « **Reply #4 on:** May 30, 2019, 04:03:44 PM »

I agree with clark. TMS acetylene is simple to handle, and easy to cleave the TMS.

rolnor · « **Reply #5 on:** May 30, 2019, 04:18:25 PM »

My thought was that harmonic_op would think of TMS-acetylene him/herself?

Topic: Phenyl acetylene (Read 1252 times)

harmonic_op

Phenyl acetylene

rolnor

Re: Phenyl acetylene

harmonic_op

Re: Phenyl acetylene

clarkstill

Re: Phenyl acetylene

wildfyr

Re: Phenyl acetylene

rolnor

Re: Phenyl acetylene

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