Yes... please, take a look in "catalysis communications, 2008, 9, 2154-2157"

cheers!!

Zhang

You wrote: 1- Will the -COOH groups interfere with the coupling?

The answer is NO

You wrote: 2- Could you please give me some advice?

The answer is, You can perform the coupling between your acetylenic carbon and the aryl iodide in the presence of the COOH group. See,

--- Moser, Heinz et al  PCT Int. Appl., 2008154642, 18 Dec 2008

Synthesis of 4-(4-formyl-phenylethynyl)-benzoic acid (2) A solution of compound 1 (1.46 g, 10 mmol), 4-iodobenzaldehyde (2.32 g, 10 mmol) and diisopropylamine (3 ml) in THF (6 ml) was purged for 10 min with dry nitrogen. A mixture of PdCl2(PPh3)2 (210 mg, 0.03 mmol), and Cul (114 mg, 0.06 mmol) was added and reaction mixture was stirred at ambient temperature overnight. Formed precipitate was filtrated. Filtrate was evaporated in vacuum. Residue was dissolved in EtOAc (100 ml) and stirred with 5% aq. NaHCO3 (30 ml). Formed precipitate was filtrated, washed with water, EtOAc, ether and dried in vacuum to provide target product (2.4 g, 96%) as off-white solid 4-(4-formyl-phenylethynyl)-benzoic acid (2), yield 2.4 g, 96%

Also see,

---  Burrows, Andrew D. et al,  CrystEngComm, 14(1), 188-192; 2012

--- van der Lit, Joost et al,  Journal of Physical Chemistry C, 120(1), 318-323; 2016

--- Dibowski, Harald and Schmidtchen, Franz P.,  Tetrahedron, 51(8), 2325-30; 1995

---  Gluyas, Josef B. G. et al,  Organic & Biomolecular Chemistry, 10(34), 6914-6929; 2012

--- Safaei-Ghomi, Javad and Akbarzadeh, Zeinab, Ultrasonics Sonochemistry, 22, 365-370; 2015

Good luck

Dear Carson, thanks for providing the article. It is exactly what I need. Cheers!

Dear Amer. Thank you very much for your considerate answer. The experimental details are very instructive to me. The references are very helpful. Good luck!

I think there may be some influence on the reaction. When I took the reaction by using iodobenzene with -COOH, the yield is obviously lower than the reaction using iodobenzene with other functional groups.