{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,11,4]],"date-time":"2026-11-04T17:41:38Z","timestamp":1793814098238,"version":"4.6.1"},"reference-count":26,"publisher":"Frontiers Media SA","license":[{"start":{"date-parts":[[2022,4,7]],"date-time":"2022-04-07T00:00:00Z","timestamp":1649289600000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"content-domain":{"domain":["frontiersin.org"],"crossmark-restriction":true},"short-container-title":["Front. Chem."],"abstract":"<jats:p>Practical approaches for chemoselective mono-bromination, di-bromination, and tetra-bromination of terminal alkynes to generate 1-bromoalkynes, 1,2-dibromoalkenes, \u03b1,\u03b1-dibromoketones, and 1,1,2,2-tetrabromoalkanes based on efficient oxidative brominations mediated by a hypervalent iodine reagent have been developed. Chemoselective bromination can be realized under mild conditions by altering the bromine source. The tetrabutylammonium bromide (TBAB)\/(diacetoxyiodo)benzene (PIDA) system is specific for mono-bromination to provide 1-bromoalkynes, while the NaBr\/PIDA system is selective toward di-bromination to achieve 1,2-dibromoalkenes. When a certain amount of water was added to the NaBr\/PIDA system, a different di-bromination product, \u03b1,\u03b1-dibromo ketones, was generated. Tetra-bromination of terminal alkynes provides an efficient protocol for the synthesis of 1,1,2,2-tetrabromoalkanes in a system with an excess loading of NaBr\/PIDA in one pot. This bromination affords good yields (up to 99%) with excellent chemoselectivity (up to 100%). These methods can be applied to the efficient chemoselective synthesis of bromide derivatives, intermediates, and related biologically active compounds.<\/jats:p>","DOI":"10.3389\/fchem.2022.879789","type":"journal-article","created":{"date-parts":[[2022,4,7]],"date-time":"2022-04-07T01:10:05Z","timestamp":1649293805000},"update-policy":"https:\/\/doi.org\/10.3389\/crossmark-policy","source":"Crossref","is-referenced-by-count":5,"title":["Hypervalent Iodine-Mediated Chemoselective Bromination of Terminal Alkynes"],"prefix":"10.3389","volume":"10","author":[{"given":"Youzhi","family":"Li","sequence":"first","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Xuemei","family":"Chen","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Daya","family":"Huang","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Zhenming","family":"Xie","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Yan","family":"Liu","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1965","published-online":{"date-parts":[[2022,4,7]]},"reference":[{"key":"B1","doi-asserted-by":"publisher","first-page":"864","DOI":"10.2174\/157017941006140206102818","article-title":"Bromide Bromate Couple of Varying Ratios for Bromination, Vicinal Functionalization and Oxidation in a Clean Manner","volume":"10","author":"Adimurthym","year":"2013","journal-title":"Curr. 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