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To date, the conceptual and methodological development of metathesis transformations has been focused predominantly on carbon\u2013carbon unsaturated bonds, and strategies that combine unsaturated bond reorganization with the direct incorporation of heteroatoms remain rare. Additionally, the established metathesis methodologies have been developed typically within the framework of transition metal catalysis, and transition metal\u2010free alternatives are scarcely explored. Here, we demonstrate that borata\u2010alkenes can serve as non\u2010metal alkylidene surrogates to enable a transition metal\u2010free hetero\u2010enyne metathesis to access cyclopentene derivatives. This process accommodates diverse electrophiles and can be integrated into cascade sequences, allowing three\u2010 and four\u2010component couplings from readily accessible 1,1,1\u2010triborylalkanes. The resulting chemodivergent products include cyclopentenyl boronic esters, geminal borylsilylalkanes, conjugated dienes, and, in a sequential four\u2010component variant, highly substituted ketones and enol ethers. Mechanistic studies and density functional theory (DFT) calculations support a borata\u2010alkene\u2010mediated metathesis pathway, establishing a transition metal\u2010free approach for cyclopentene synthesis via carbon\u2013carbon bond reorganization.<\/jats:p>","DOI":"10.1002\/anie.5554467","type":"journal-article","created":{"date-parts":[[2026,6,23]],"date-time":"2026-06-23T08:04:55Z","timestamp":1782201895000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":0,"title":["Transition Metal\u2010Free Borata\u2010Alkene\/Alkyne Metathesis Enables Access to Cyclopentenes"],"prefix":"10.1002","volume":"65","author":[{"given":"Wenke","family":"Dong","sequence":"first","affiliation":[{"name":"College of Chemistry and Chemical Engineering Zhoukou Normal University  Zhoukou Henan Peoples's Republic of China"},{"name":"State Key Laboratory of Chemo and Biosensing College of Chemistry and Chemical Engineering Hunan University  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