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Topic: Sonogashira coupling: Functional group tolerance  (Read 5853 times)

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Offline asa029

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Sonogashira coupling: Functional group tolerance
« on: August 26, 2011, 09:52:56 AM »
Does anyone have any idea about the functional group tolerance in the sonogashira coupling? I have tried to find any articles/reviews on the subject, but to no avail. Both articles and input on the subject is appreciated:D
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Offline opsomath

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Re: Sonogashira coupling: Functional group tolerance
« Reply #1 on: August 26, 2011, 09:57:11 AM »
It's pretty broad, in my limited experience. I have definitely done it in the presence of an unprotected aryl amine, and IIRC a phenol as well. I seem to recall a thread on chemmit where somebody did a carboxylic acid too.
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Offline nox

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Re: Sonogashira coupling: Functional group tolerance
« Reply #2 on: August 26, 2011, 06:03:23 PM »
Very broad indeed. From personal experience, alkyl, alkoxy, cyano, nitro, aryl ketone, tertiary aryl amine, free alcohol groups are all tolerated. If you have multiple halogens present on your substrate, you could even do selective coupling to only the iodide/bromide under the right conditions.
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