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A distorted square planar geometry for Pd-C2 and Pd-C3 was confirmed by single-crystal X-ray diffraction. The palladium(II) complexes show a remarkably higher catalytic activity and selectivity, compared to the literature data, in carbonylative Sonogashira coupling reactions of aryl iodides and aryl diiodides with aryl alkynes, alkyl alkynes, and dialkynes. Excellent yields with as low as 0.03 mol % loading of the catalyst were obtained. In the series of benzimidazolium (NHC) precursors, the 1H NMR signals of the \u03b1 hydrogen show a consistent probing of the N-substituent donor strength. The density functional theory (DFT) quantum mechanical descriptors of the frontier orbitals were calculated. A linear correlation of the calculated absolute softness of the complexes versus the calculated percent buried volume (%Vbur) of their corresponding ligands was obtained. The catalytic activity experimental data are consistent with the hard soft acid base (HSAB)-predicted high affinity of the softest Pd-C3 complex for soft substrates, such as aryl iodides.<\/jats:p>","DOI":"10.1021\/acsomega.0c02413","type":"journal-article","created":{"date-parts":[[2020,8,18]],"date-time":"2020-08-18T10:40:45Z","timestamp":1597747245000},"page":"23687-23702","source":"Crossref","is-referenced-by-count":19,"title":["Soft Heteroleptic N-Heterocyclic Carbene Palladium(II)\nSpecies for Efficient Catalytic Routes to Alkynones via Carbonylative\nSonogashira Coupling"],"prefix":"10.1021","volume":"5","author":[{"given":"Waseem","family":"Mansour","sequence":"first","affiliation":[{"name":"King Fahd University of Petroleum & Minerals , , ,","place":["Dhahran, Saudi Arabia, 31261"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Rami","family":"Suleiman","sequence":"additional","affiliation":[{"name":"King Fahd University of Petroleum & Minerals , , ,","place":["Dhahran, Saudi Arabia, 31261"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Mohammed","family":"Fettouhi","sequence":"additional","affiliation":[{"name":"King Fahd University of Petroleum & Minerals , , ,","place":["Dhahran, Saudi Arabia, 31261"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-4005-6386","authenticated-orcid":true,"given":"Bassam","family":"El Ali","sequence":"additional","affiliation":[{"name":"King Fahd University of Petroleum & Minerals , , ,","place":["Dhahran, Saudi Arabia, 31261"]}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"316","published-online":{"date-parts":[[2020,8,18]]},"reference":[{"key":"2026090206555590600_cit1","doi-asserted-by":"publisher","first-page":"6951","DOI":"10.1002\/anie.200501703","article-title":"Concise\nsyntheses of meridianins by carbonylative alkynylation and a four-component\npyrimidine synthesis","volume":"44","author":"Karpov","year":"2005","journal-title":"Angew. 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