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Herein, we report a practical and versatile method for the synthesis of a variety of monophosphorus compounds directly from the bench\u2010stable allotrope red phosphorus (P<jats:sub>red<\/jats:sub>). The relatively inert P<jats:sub>red<\/jats:sub> was productively functionalised by using the cheap and readily available radical reagent tri\u2010<jats:italic>n<\/jats:italic>\u2010butyltin hydride, and subsequent treatment with electrophiles yields useful P<jats:sub>1<\/jats:sub> compounds. Remarkably, these transformations require only modest inert\u2010atmosphere techniques and use only reagents that are inexpensive and commercially available, making this a convenient and practical methodology accessible in most laboratory settings.<\/jats:p>","DOI":"10.1002\/chem.202202456","type":"journal-article","created":{"date-parts":[[2022,8,31]],"date-time":"2022-08-31T11:24:45Z","timestamp":1661945085000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":16,"title":["Hydrostannylation of Red Phosphorus: A Convenient Route to Monophosphines"],"prefix":"10.1002","volume":"28","author":[{"given":"Jose","family":"Cammarata","sequence":"first","affiliation":[{"name":"Institute of Inorganic Chemistry University of Regensburg  93040 Regensburg Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-7826-9833","authenticated-orcid":false,"given":"Daniel J.","family":"Scott","sequence":"additional","affiliation":[{"name":"Department of Chemistry University of Oxford  OX1 3TA Oxford UK"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-4066-6483","authenticated-orcid":false,"given":"Robert","family":"Wolf","sequence":"additional","affiliation":[{"name":"Institute of Inorganic Chemistry University of Regensburg  93040 Regensburg Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2022,10,6]]},"reference":[{"key":"e_1_2_3_1_1","unstructured":"\u00a0"},{"key":"e_1_2_3_2_2","volume-title":"Phosphorus. 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However for these systems we have thus far only been able to achieve low conversions (<20\u2009% (Bu3Sn)xPH3-x). See Section\u20055 in the Supporting Information for more details."},{"key":"e_1_2_3_45_1","unstructured":"As in the case using P4 irradiation with LED light is proposed to induce the formation of an initial Bu3Sn\u22c5 radical which initiates the chain reaction. However the precise details of this initiation are currently unclear and remain under investigation."},{"key":"e_1_2_3_46_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0022-328X(00)98800-4"},{"key":"e_1_2_3_47_1","unstructured":"The transformation of Bu3SnCl into Bu3SnH or Bu3SnOMe can be achieved in excellent yields by treatment with NaBH4or NaOMe respectively see:"},{"key":"e_1_2_3_48_2","first-page":"10","volume":"9","author":"Heumann L. V.","year":"2007","journal-title":"Org. Lett."},{"key":"e_1_2_3_49_2","doi-asserted-by":"publisher","DOI":"10.1021\/om000397f"},{"key":"e_1_2_3_50_1","doi-asserted-by":"publisher","DOI":"10.1021\/ie4036753"},{"key":"e_1_2_3_51_1","doi-asserted-by":"publisher","DOI":"10.1002\/cber.19811140220"},{"key":"e_1_2_3_52_1","unstructured":"We have previously demonstrated that the various components of the (Bu3Sn)xPH3\u2212xmixture including (Bu3Sn)3P are sufficiently air-stable to allow them to be left under air overnight without appreciable changeversusequivalent storage under N2(see ref. 13). 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