{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,1,16]],"date-time":"2026-01-16T16:24:19Z","timestamp":1768580659330,"version":"3.49.0"},"reference-count":80,"publisher":"Wiley","issue":"23","license":[{"start":{"date-parts":[[2018,6,1]],"date-time":"2018-06-01T00:00:00Z","timestamp":1527811200000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"funder":[{"DOI":"10.13039\/501100002341","name":"Suomen Akatemia","doi-asserted-by":"publisher","award":["287954"],"award-info":[{"award-number":["287954"]}],"id":[{"id":"10.13039\/501100002341","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100002341","name":"Suomen Akatemia","doi-asserted-by":"publisher","award":["294067"],"award-info":[{"award-number":["294067"]}],"id":[{"id":"10.13039\/501100002341","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100001871","name":"Funda\u00e7\u00e3o para a Ci\u00eancia e a Tecnologia","doi-asserted-by":"publisher","award":["UID\/QUI\/00100\/2013"],"award-info":[{"award-number":["UID\/QUI\/00100\/2013"]}],"id":[{"id":"10.13039\/501100001871","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":["chemistry-europe.onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["Eur J Org Chem"],"published-print":{"date-parts":[[2018,6,22]]},"abstract":"<jats:p>A newly developed stable chlorohydrosilane derived from pinacol is herein described. This was successfully used in the reduction of salicylaldehydes in reasonable to excellent yields (51\u201397\u2009%). The ability of the hydrosilane to react as a reducing agent is increased upon the in situ formation of a trialkoxyhydrosilane and activation with a Lewis base, as further indicated by density functional theory studies. 1,3\u2010Dimethyl\u20103,4,5,6\u2010tetrahydro\u20102(1<jats:italic>H<\/jats:italic>)\u2010pyrimidinone (DMPU) was identified to be a suitable catalyst for this metal\u2010free reduction, promoting the regio\u2010 and chemoselective reduction of aldehydes in <jats:italic>ortho<\/jats:italic>\u2010position to phenols, despite the presence of vicinal ketones. The performance of pinacol\u2010derived chlorohydrosilane in the reduction of salicylaldehydes was further observed to be superior to that of well\u2010established commercially available chlorohydrosilanes.<\/jats:p>","DOI":"10.1002\/ejoc.201800544","type":"journal-article","created":{"date-parts":[[2018,6,1]],"date-time":"2018-06-01T10:11:51Z","timestamp":1527847911000},"page":"2910-2917","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":11,"title":["Lewis Base Catalyzed Intramolecular Reduction of Salicylaldehydes by Pinacol\u2010Derived Chlorohydrosilane"],"prefix":"10.1002","volume":"2018","author":[{"given":"Benedicta","family":"Assoah","sequence":"first","affiliation":[{"name":"Laboratory of Chemistry and Bioengineering Tampere University of Technology  Korkeakoulunkatu 8 33101 Tampere Finland"}]},{"given":"Jo\u00e3o R.","family":"Vale","sequence":"additional","affiliation":[{"name":"Laboratory of Chemistry and Bioengineering Tampere University of Technology  Korkeakoulunkatu 8 33101 Tampere Finland"},{"name":"Instituto de Investiga\u00e7\u00e3o do Medicamento (iMed.ULisboa) Faculdade de Farm\u00e1cia Universidade de Lisboa  Av. Prof. Gama Pinto 1649\u2010003 Lisboa Portugal"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-8038-1314","authenticated-orcid":false,"given":"Elina","family":"Kalenius","sequence":"additional","affiliation":[{"name":"University of Jyv\u00e4skyl\u00e4 Department of Chemistry Nanoscience Center  Jyv\u00e4skyl\u00e4 Finland"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-5841-3519","authenticated-orcid":false,"given":"Luis F.","family":"Veiros","sequence":"additional","affiliation":[{"name":"Centro de Qu\u00edmica Estrutural Instituto Superior T\u00e9cnico Universidade de Lisboa  Av. Rovisco Pais No. 1 1049\u2010001 Lisboa Portugal"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-2414-9064","authenticated-orcid":false,"given":"Nuno R.","family":"Candeias","sequence":"additional","affiliation":[{"name":"Laboratory of Chemistry and Bioengineering Tampere University of Technology  Korkeakoulunkatu 8 33101 Tampere Finland"}]}],"member":"311","published-online":{"date-parts":[[2018,6]]},"reference":[{"key":"e_1_2_6_2_1","doi-asserted-by":"publisher","DOI":"10.1002\/9783527622115"},{"key":"e_1_2_6_2_2","volume-title":"Comprehensive Organic Synthesis II (Second Edition)","author":"Knochel P.","year":"2014"},{"key":"e_1_2_6_3_1","volume-title":"Ionic and Organometallic\u2010Catalyzed Organosilane Reductions, vol. 71","author":"Larson G. L."},{"key":"e_1_2_6_3_2","doi-asserted-by":"publisher","DOI":"10.1021\/ar7001655"},{"key":"e_1_2_6_3_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201100145"},{"key":"e_1_2_6_3_4","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201100145"},{"key":"e_1_2_6_4_1","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.201700374"},{"key":"e_1_2_6_4_2","doi-asserted-by":"publisher","DOI":"10.1055\/s-0036-1590838"},{"key":"e_1_2_6_4_3","doi-asserted-by":"publisher","DOI":"10.1021\/jo501505j"},{"key":"e_1_2_6_4_4","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201501729"},{"key":"e_1_2_6_4_5","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201501729"},{"key":"e_1_2_6_5_1","doi-asserted-by":"publisher","DOI":"10.1007\/978-1-4020-8172-9_9"},{"key":"e_1_2_6_6_1","doi-asserted-by":"publisher","DOI":"10.1021\/jo00396a056"},{"key":"e_1_2_6_6_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0022-328X(00)87264-2"},{"key":"e_1_2_6_7_1","doi-asserted-by":"publisher","DOI":"10.1039\/c39810000121"},{"key":"e_1_2_6_7_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol1024635"},{"key":"e_1_2_6_7_3","doi-asserted-by":"publisher","DOI":"10.1021\/jo401293a"},{"key":"e_1_2_6_8_1","doi-asserted-by":"publisher","DOI":"10.1021\/om034285a"},{"key":"e_1_2_6_8_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.jorganchem.2006.10.025"},{"key":"e_1_2_6_8_3","doi-asserted-by":"publisher","DOI":"10.1021\/om801160j"},{"key":"e_1_2_6_8_4","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201605198"},{"key":"e_1_2_6_8_5","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201605198"},{"key":"e_1_2_6_9_1","doi-asserted-by":"publisher","DOI":"10.1021\/cs300848h"},{"key":"e_1_2_6_9_2","doi-asserted-by":"publisher","DOI":"10.1021\/om300654q"},{"key":"e_1_2_6_10_1","doi-asserted-by":"publisher","DOI":"10.1039\/B703488C"},{"key":"e_1_2_6_10_2","doi-asserted-by":"publisher","DOI":"10.1021\/op2003826"},{"key":"e_1_2_6_11_1","doi-asserted-by":"publisher","DOI":"10.1039\/C4CS00451E"},{"key":"e_1_2_6_11_2","doi-asserted-by":"publisher","DOI":"10.1039\/cs9972600345"},{"key":"e_1_2_6_12_1","doi-asserted-by":"publisher","DOI":"10.1021\/jo00932a015"},{"key":"e_1_2_6_13_1","doi-asserted-by":"publisher","DOI":"10.1002\/adsc.200800815"},{"key":"e_1_2_6_14_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200604943"},{"key":"e_1_2_6_14_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200604943"},{"key":"e_1_2_6_15_1","doi-asserted-by":"publisher","DOI":"10.1021\/jo00381a048"},{"key":"e_1_2_6_16_1","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201403497"},{"key":"e_1_2_6_17_1","doi-asserted-by":"publisher","DOI":"10.1021\/jo00258a003"},{"key":"e_1_2_6_17_2","doi-asserted-by":"publisher","DOI":"10.1139\/v06-116"},{"key":"e_1_2_6_17_3","doi-asserted-by":"publisher","DOI":"10.1039\/C4RA13090A"},{"key":"e_1_2_6_18_1","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.201601256"},{"key":"e_1_2_6_19_1","doi-asserted-by":"publisher","DOI":"10.1246\/cl.1996.407"},{"key":"e_1_2_6_20_1","doi-asserted-by":"publisher","DOI":"10.1039\/C39860000831"},{"key":"e_1_2_6_20_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4020(01)86634-5"},{"key":"e_1_2_6_20_3","doi-asserted-by":"publisher","DOI":"10.1039\/p19910001383"},{"key":"e_1_2_6_21_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja00033a074"},{"key":"e_1_2_6_22_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4020(01)91219-0"},{"key":"e_1_2_6_23_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja00095a004"},{"key":"e_1_2_6_23_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00046a054"},{"key":"e_1_2_6_23_3","doi-asserted-by":"publisher","DOI":"10.1021\/ja0264908"},{"key":"e_1_2_6_24_1","first-page":"1727","author":"Rendler S.","year":"2005","journal-title":"Synthesis"},{"key":"e_1_2_6_24_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr00020a003"},{"key":"e_1_2_6_25_1","doi-asserted-by":"publisher","DOI":"10.1002\/open.201402066"},{"key":"e_1_2_6_25_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.ejmech.2016.05.024"},{"key":"e_1_2_6_25_3","doi-asserted-by":"publisher","DOI":"10.1002\/cmdc.201600244"},{"key":"e_1_2_6_26_1","doi-asserted-by":"publisher","DOI":"10.1039\/C7GC01289F"},{"key":"e_1_2_6_26_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.bmcl.2016.03.039"},{"key":"e_1_2_6_26_3","doi-asserted-by":"publisher","DOI":"10.1021\/jo001362s"},{"key":"e_1_2_6_26_4","doi-asserted-by":"publisher","DOI":"10.1021\/jo00082a006"},{"key":"e_1_2_6_26_5","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.201700887"},{"key":"e_1_2_6_26_6","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(99)01902-4"},{"key":"e_1_2_6_27_1","doi-asserted-by":"publisher","DOI":"10.1021\/ar50039a003"},{"key":"e_1_2_6_28_1","doi-asserted-by":"publisher","DOI":"10.1021\/jo5016568"},{"key":"e_1_2_6_28_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.5b01536"},{"key":"e_1_2_6_29_1","volume-title":"Encyclopedia of Reagents for Organic Synthesis","author":"Beck A. K.","year":"2001"},{"key":"e_1_2_6_30_1","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.201600616"},{"key":"e_1_2_6_31_1","doi-asserted-by":"publisher","DOI":"10.1039\/p19800001862"},{"key":"e_1_2_6_31_2","doi-asserted-by":"publisher","DOI":"10.1039\/C6NJ02815B"},{"key":"e_1_2_6_32_1","volume-title":"Density Functional Theory of Atoms and Molecules","author":"Parr R. G.","year":"1989"},{"key":"e_1_2_6_32_2","unstructured":"b) DFT calculations at the M06\u20132X\/6\u2013311++G(d p)\/\/PBE0\/6\u201331G(d p) level were performed using theGAUSSIAN 09package. Solvent effects (CH2Cl2) were considered in all calculations by means of the PCM model with SMD radii. A complete account of the computational details the corresponding list of references are provided as SI"},{"key":"e_1_2_6_33_1","doi-asserted-by":"publisher","DOI":"10.1039\/b926864b"},{"key":"e_1_2_6_33_2","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.200500490"},{"key":"e_1_2_6_33_3","doi-asserted-by":"publisher","DOI":"10.1039\/C4OB00228H"},{"key":"e_1_2_6_33_4","doi-asserted-by":"publisher","DOI":"10.1002\/cmdc.201300048"},{"key":"e_1_2_6_33_5","doi-asserted-by":"publisher","DOI":"10.1002\/(SICI)1099-0690(199805)1998:5<837::AID-EJOC837>3.0.CO;2-7"},{"key":"e_1_2_6_33_6","doi-asserted-by":"publisher","DOI":"10.1002\/cphc.201600141"},{"key":"e_1_2_6_33_7","doi-asserted-by":"publisher","DOI":"10.1039\/C4DT03337J"},{"key":"e_1_2_6_33_8","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201600223"},{"key":"e_1_2_6_33_9","doi-asserted-by":"publisher","DOI":"10.1007\/s11164-016-2606-8"},{"key":"e_1_2_6_33_10","doi-asserted-by":"publisher","DOI":"10.1021\/jm0613267"},{"key":"e_1_2_6_33_11","doi-asserted-by":"publisher","DOI":"10.1016\/j.jorganchem.2015.05.002"},{"key":"e_1_2_6_33_12","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201304654"},{"key":"e_1_2_6_33_13","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201304654"}],"container-title":["European Journal of Organic Chemistry"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.wiley.com\/onlinelibrary\/tdm\/v1\/articles\/10.1002%2Fejoc.201800544","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/ejoc.201800544","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,15]],"date-time":"2025-10-15T12:26:41Z","timestamp":1760531201000},"score":1,"resource":{"primary":{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/10.1002\/ejoc.201800544"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2018,6]]},"references-count":80,"journal-issue":{"issue":"23","published-print":{"date-parts":[[2018,6,22]]}},"alternative-id":["10.1002\/ejoc.201800544"],"URL":"https:\/\/doi.org\/10.1002\/ejoc.201800544","archive":["Portico"],"relation":{},"ISSN":["1434-193X","1099-0690"],"issn-type":[{"value":"1434-193X","type":"print"},{"value":"1099-0690","type":"electronic"}],"subject":[],"published":{"date-parts":[[2018,6]]},"assertion":[{"value":"2018-04-05","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2018-06-01","order":3,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}]}}