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The alkynes underwent cyclization on M via a \u201cnon\u2010vinylidene\u201d pathway at lower temperatures, resulting in alkenyl intermediates which might further metallacyclize to give metallapyrroloindolizines. Conversely, reactions at higher temperatures induced alkyne cyclization on M via a \u201cvinylidene\u201d pathway, affording cyclic oxacarbene complexes. Additionally, a rare decyclization mechanism was observed during the transformation of a metallacyclization\u2010resistant alkenyl complex into a cyclic oxacarbene complex. DFT calculations were employed to validate the experimental findings. Overall, these results not only provide insights into controlling alkyne activation pathways, but also offer new strategies for preparing metalated heterocyclic and metallacyclic complexes.<\/jats:p>","DOI":"10.1002\/chem.202301292","type":"journal-article","created":{"date-parts":[[2023,5,17]],"date-time":"2023-05-17T23:34:41Z","timestamp":1684366481000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":3,"title":["Cyclization, Decyclization, and Metallacyclization of Pyridine\u2010Substituted Homopropargylic Alcohols on Ruthenium(II) and Osmium(II) Centers"],"prefix":"10.1002","volume":"29","author":[{"ORCID":"https:\/\/orcid.org\/0000-0003-0907-5634","authenticated-orcid":false,"given":"Hau\u2010Lam","family":"Shek","sequence":"first","affiliation":[{"name":"Department of Chemistry City University of Hong Kong  Tat Chee Avenue Kowloon Hong Kong SAR"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-1444-6989","authenticated-orcid":false,"given":"Chi\u2010Fung","family":"Yeung","sequence":"additional","affiliation":[{"name":"Department of Chemistry City University of Hong Kong  Tat Chee Avenue Kowloon Hong Kong SAR"},{"name":"State Key Laboratory of Terahertz and Millimeter Waves City University of Hong Kong  Tat Chee Avenue Kowloon Hong Kong SAR"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-0482-1362","authenticated-orcid":false,"given":"Lai\u2010Hon","family":"Chung","sequence":"additional","affiliation":[{"name":"School of Chemical Engineering and Light Industry Guangdong University of Technology  GuangZhou P.\u2005R. 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