{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,26]],"date-time":"2026-09-26T11:29:00Z","timestamp":1790422140704,"version":"4.1.0"},"reference-count":52,"publisher":"Wiley","issue":"6","license":[{"start":{"date-parts":[[2018,1,15]],"date-time":"2018-01-15T00:00:00Z","timestamp":1515974400000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"name":"Royal Society for a University Research Fellowship","award":["UF\/110061"],"award-info":[{"award-number":["UF\/110061"]}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Adv Synth Catal"],"published-print":{"date-parts":[[2018,3,20]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>Despite the ever\u2010broadening applications of main\u2010group \u2018frustrated Lewis pair\u2019 (FLP) chemistry to both new and established reactions, their typical intolerance of water, especially at elevated temperatures (&gt;100\u2009\u00b0C), represents a key barrier to their mainstream adoption. Herein we report that FLPs based on the Lewis acid <jats:sup>i<\/jats:sup>Pr<jats:sub>3<\/jats:sub>SnOTf are moisture tolerant in the presence of moderately strong nitrogenous bases, even under high temperature regimes, allowing them to operate as simple and effective catalysts for the reductive amination of organic carbonyls, including for challenging bulky amine and carbonyl substrate partners.<\/jats:p><jats:p><jats:boxed-text content-type=\"graphic\" position=\"anchor\"><jats:graphic xmlns:xlink=\"http:\/\/www.w3.org\/1999\/xlink\" mimetype=\"image\/png\" position=\"anchor\" specific-use=\"enlarged-web-image\" xlink:href=\"graphic\/adsc201701418-toc-0001-m.png\"><jats:alt-text>magnified image<\/jats:alt-text><\/jats:graphic><\/jats:boxed-text>\n<\/jats:p>","DOI":"10.1002\/adsc.201701418","type":"journal-article","created":{"date-parts":[[2017,12,28]],"date-time":"2017-12-28T02:00:49Z","timestamp":1514426449000},"page":"1066-1071","source":"Crossref","is-referenced-by-count":47,"title":["Direct Reductive Amination of Carbonyl Compounds Catalyzed by a Moisture Tolerant Tin(IV) Lewis Acid"],"prefix":"10.1002","volume":"360","author":[{"given":"Joshua S.","family":"Sapsford","sequence":"first","affiliation":[{"name":"Department of Chemistry Imperial College London  London SW7 2AZ UK"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Daniel J.","family":"Scott","sequence":"additional","affiliation":[{"name":"Department of Chemistry Imperial College London  London SW7 2AZ UK"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Nathan J.","family":"Allcock","sequence":"additional","affiliation":[{"name":"Department of Chemistry Imperial College London  London SW7 2AZ UK"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Matthew J.","family":"Fuchter","sequence":"additional","affiliation":[{"name":"Department of Chemistry Imperial College London  London SW7 2AZ UK"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Christopher J.","family":"Tighe","sequence":"additional","affiliation":[{"name":"Department of Chemical Engineering Imperial College London  London SW7 2AZ UK"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Andrew E.","family":"Ashley","sequence":"additional","affiliation":[{"name":"Department of Chemistry Imperial College London  London SW7 2AZ UK"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2018,1,15]]},"reference":[{"key":"e_1_2_2_2_1","unstructured":"\u00a0"},{"key":"e_1_2_2_3_2","doi-asserted-by":"publisher","DOI":"10.1126\/science.1134230"},{"key":"e_1_2_2_4_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja067961j"},{"key":"e_1_2_2_5_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200700151"},{"key":"e_1_2_2_6_2","doi-asserted-by":"publisher","DOI":"10.1039\/b718598g"},{"key":"e_1_2_2_7_2","doi-asserted-by":"publisher","DOI":"10.1039\/b801806e"},{"key":"e_1_2_2_8_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200905466"},{"key":"e_1_2_2_9_2","doi-asserted-by":"publisher","DOI":"10.1038\/nchem.1693"},{"key":"e_1_2_2_10_2","doi-asserted-by":"publisher","DOI":"10.1126\/science.aab3591"},{"key":"e_1_2_2_11_1","unstructured":"\u00a0"},{"key":"e_1_2_2_12_2","doi-asserted-by":"publisher","DOI":"10.1021\/ic200663v"},{"key":"e_1_2_2_13_2","volume-title":"Frustrated Lewis Pairs, Vols. 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An independent experiment mixing1 Col and H2O (1:1:10) in DCB showed that free H2O displays a resonance at \u03b4=5.16\u2005ppm whereas H2O bound to the Sn centre appears at \u03b4=4.90\u2005ppm (correlated to a broad119Sn{1H} NMR resonance at \u03b4=35\u2005ppm). A1H NOESY experiment reveals the latter signal to display though\u2212space coupling between H2O and the Sn(CH(CH3)2)3protons of the LA and to the \u03b1-CH3protons in the LB. This is consistent with H-bonding between Col and coordinated H2O possibly formulated as [iPr3Sn\u22c5(H2O)(HO\u22c5\u22c5\u22c5H-Col)]+or [iPr3Sn\u22c5(H2O)(HOH\u22c5\u22c5\u22c5Col)]+ and indicates that the Br\u00f8nsted acidity of [Col-H]+and [iPr3Sn\u22c52H2O]+are very similar. The observed1H and119Sn{1H} NMR chemical shifts were found to vary depending on the concentration of H2O and the identity of the LB present which explains the small chemical shift range seen in the RA experiments. See SI for full details."},{"key":"e_1_2_2_47_1","doi-asserted-by":"publisher","DOI":"10.1039\/p29910000073"},{"key":"e_1_2_2_48_1","unstructured":"The failure of these ketones to undergo discernible reduction to the respective alcohols in these reactions reflects the greater difficulty of hydrogenating these C=O bondsvsimines using1 which has previously required longer reaction times (>30\u2005h for Me2CO; see ref. 27) and more weakly basic conditions (e.\u2009g. Col) than those used for the synthesis of3\u2009i."},{"key":"e_1_2_2_49_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200800935"},{"key":"e_1_2_2_50_1","doi-asserted-by":"publisher","DOI":"10.1002\/1615-4169(200212)344:10<1037::AID-ADSC1037>3.0.CO;2-3"},{"key":"e_1_2_2_51_1","unstructured":"For comparison the synthesis of3\u2009busing the protocol of So\u00f3set\u2005al. (ref. 11) achieved 85% conversion in 72\u2005h."},{"key":"e_1_2_2_52_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201405531"}],"container-title":["Advanced Synthesis &amp; Catalysis"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.wiley.com\/onlinelibrary\/tdm\/v1\/articles\/10.1002%2Fadsc.201701418","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/advanced.onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/adsc.201701418","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,6]],"date-time":"2025-10-06T17:40:01Z","timestamp":1759772401000},"score":1,"resource":{"primary":{"URL":"https:\/\/advanced.onlinelibrary.wiley.com\/doi\/10.1002\/adsc.201701418"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2018,1,15]]},"references-count":52,"journal-issue":{"issue":"6","published-print":{"date-parts":[[2018,3,20]]}},"alternative-id":["10.1002\/adsc.201701418"],"URL":"https:\/\/doi.org\/10.1002\/adsc.201701418","archive":["Portico"],"relation":{},"ISSN":["1615-4150","1615-4169"],"issn-type":[{"value":"1615-4150","type":"print"},{"value":"1615-4169","type":"electronic"}],"subject":[],"published":{"date-parts":[[2018,1,15]]}}}