Note that the interaction is not completed with prolong the time.
Thanks in advance
If I understand you correctly, you seem to want to prepare a 1-aryl-1-pentyne?
Since deprotection of the volatile alkyne seems problematic, I'd either follow the patent procedure of ASTRAZENECA AB (2012) (see picture) or maybe try the route via alkyne metathesis, as Fürstner A. et al. proposed in 2014 (see link).
https://dx.doi.org/10.1002/chem.201404166
thank you very much for your care Lukas Holz. As long deprotection of the volatile alkyne seems problematic. what the procedure and conditions Sonogashira cross coupling of aryl halides with Trimethylsilylacetylene without deprotection of silyl group and then protected it.
Dear Mohamed Elsebaei,
Find in attach, a doc. article on: Palladium-Catalyzed Coupling of Silyl-Acetylenes to Aryl Halides Using Microwave Irradiation
Ulrik S. Sørensen, Judith Wede, and Esteban Pombo-Villar*
Nervous System Research, Novartis Pharma AG, Basel, Switzerland
Fifth International Electronic Conference on Synthetic Organic Chemistry (ECSOC-5), http://www.mdpi.org/ecsoc-5.htm, 1-30 September 2001
In this you'll find It has previously been reported that the reaction between 2-iodobenzaldehyde and 1-phenyl-2-(trimethylsilyl)acetylene (3) in the presence of palladium acetate gives the corresponding 2-trimethylsilyl-substituted indenone 2.1 When repeating this experiment, using slightly different reaction conditions and replacing 2-iodobenzaldehyde with 2-bromobenzaldehyde, we did, however, not isolate the above mentioned indenone but rather the cross-coupling product 1 (Scheme 1).
Mohamed Elsebaei:
Silyl group may be inert under the basic conditions, use in Sonogashira cross coupling. Any palladium catalyst (2-5 mol%) with/without ligand can be used to accomplish a coupling reaction. A halo arene (1 mmol), TMS acetylene (1.1 mmol), Pd(PPh3)2Cl2 (7.2 mg), PPh3 (5.2 mg), CuI (2.0 mg) in triethylamine solvent (20-30 ml) (reflux) would be able to produce the coupled product. Consecutively, deprotection can be worked out.
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