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This idea can also be extended to stabilize other high\u2010coordinated p\u2010block element species. Herein, we synthesized two novel polycyclic organophosphorus heterocycles via Staudinger\u2010type annulations. Reactions of either <jats:italic>ortho<\/jats:italic>\u2010phosphinoarenesulfonyl fluorides <jats:bold>1<\/jats:bold> or <jats:italic>ortho<\/jats:italic>\u2010phosphinobenzoic acid methyl esters <jats:bold>4<\/jats:bold> with <jats:italic>ortho<\/jats:italic>\u2010azidophenols <jats:bold>2<\/jats:bold> gave rise to penta\u2010coordinated P(V) heterocycles, benzo\u2010benzo\u20101,2,3\u2010thiazaphospholo\u20101,3,2\u2010oxazaphosphole (<jats:bold>B\u2010B\u2010TAP\u2010OAP<\/jats:bold>) <jats:bold>3<\/jats:bold> and benzo\u2010benzo\u20101,2\u2010azaphospholo\u20101,3,2\u2010oxazaphosphol\u201012\u2010one (<jats:bold>B\u2010B\u2010AP\u2010OAP<\/jats:bold>) <jats:bold>5<\/jats:bold> in satisfactory yields. It is remarkable that heterocycles <jats:bold>3<\/jats:bold> and <jats:bold>5<\/jats:bold> are both bench\u2010stable and exhibit considerable stability in a 10\u2009% aqueous tetrahydrofuran solution. Preliminary computational studies disclosed that the formation of nitrogen gas is the key driving force for the annulations. In addition, the formation of a strong Si\u2212F bond is another contributor to the annulation of <jats:bold>1<\/jats:bold> and <jats:bold>2<\/jats:bold>.<\/jats:p>","DOI":"10.1002\/chem.202302834","type":"journal-article","created":{"date-parts":[[2023,12,23]],"date-time":"2023-12-23T15:05:00Z","timestamp":1703343900000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":1,"title":["Synthesis of Bench\u2010stable Polycyclic Organophosphorus Heterocycles via Staudinger\u2010type Annulations of <i>ortho<\/i>\u2010Azidophenols"],"prefix":"10.1002","volume":"30","author":[{"given":"Zhenguo","family":"Wang","sequence":"first","affiliation":[{"name":"School of Chemistry Sun Yat-sen University  Guangzhou 510275 P. R. China"},{"name":"PCFM Lab and GDHPRC Lab Sun Yat-sen University  Guangzhou 510275 P. R. 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