{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,5]],"date-time":"2026-10-05T19:37:28Z","timestamp":1791229048799,"version":"4.1.0"},"reference-count":55,"publisher":"American Chemical Society (ACS)","issue":"10","content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Org. Lett."],"published-print":{"date-parts":[[2003,5,1]]},"DOI":"10.1021\/ol034434l","type":"journal-article","created":{"date-parts":[[2003,5,8]],"date-time":"2003-05-08T05:15:06Z","timestamp":1052370906000},"page":"1773-1776","source":"Crossref","is-referenced-by-count":83,"title":["Indium-Mediated Reduction of Hydroxylamines to Amines"],"prefix":"10.1021","volume":"5","author":[{"given":"Stefano","family":"Cicchi","sequence":"first","affiliation":[{"name":"Dipartimento di Chimica Organica \u201cUgo Schiff\u201d, Universit\u00e0 di Firenze, via della Lastruccia 13, I-50019 Sesto Fiorentino (FI), Italy"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Marco","family":"Bonanni","sequence":"additional","affiliation":[{"name":"Dipartimento di Chimica Organica \u201cUgo Schiff\u201d, Universit\u00e0 di Firenze, via della Lastruccia 13, I-50019 Sesto Fiorentino (FI), Italy"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Francesca","family":"Cardona","sequence":"additional","affiliation":[{"name":"Dipartimento di Chimica Organica \u201cUgo Schiff\u201d, Universit\u00e0 di Firenze, via della Lastruccia 13, I-50019 Sesto Fiorentino (FI), Italy"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Julia","family":"Revuelta","sequence":"additional","affiliation":[{"name":"Dipartimento di Chimica Organica \u201cUgo Schiff\u201d, Universit\u00e0 di Firenze, via della Lastruccia 13, I-50019 Sesto Fiorentino (FI), Italy"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Andrea","family":"Goti","sequence":"additional","affiliation":[{"name":"Dipartimento di Chimica Organica \u201cUgo Schiff\u201d, Universit\u00e0 di Firenze, via della Lastruccia 13, I-50019 Sesto Fiorentino (FI), Italy"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"316","published-online":{"date-parts":[[2003,4,22]]},"reference":[{"key":"ol034434lb00001\/ol034434lb00001_1","first-page":"264","volume-title":"Green Chemistry\u2212Frontiers in Benign Chemical Syntheses and Processes","author":"Reviews","year":"1998"},{"key":"ol034434lb00002\/ol034434lb00002_1","first-page":"977","volume":"955","author":"Pitts M. R.","year":"2001","journal-title":"J. Chem. Soc., Perkin Trans. 1"},{"key":"ol034434lb00002\/ol034434lb00002_2","doi-asserted-by":"crossref","first-page":"1028","DOI":"10.1055\/s-1998-1837","author":"Moody C. J.","year":"1998","journal-title":"Synlett"},{"key":"ol034434lb00002\/ol034434lb00002_3","first-page":"1030","volume":"1029","author":"Moody C. J.","year":"1998","journal-title":"Synlett"},{"key":"ol034434lb00002\/ol034434lb00002_4","first-page":"1576","volume":"1575","author":"Moody C. J.","year":"1999","journal-title":"Synlett"},{"key":"ol034434lb00002\/ol034434lb00002_5","first-page":"1602","volume":"1601","author":"Harrison J. R.","year":"2000","journal-title":"Synlett"},{"key":"ol034434lb00002\/ol034434lb00002_6","doi-asserted-by":"crossref","first-page":"2113","DOI":"10.1039\/a806530f","author":"Ranu B. C.","year":"1998","journal-title":"Chem. Commun."},{"key":"ol034434lb00002\/ol034434lb00002_7","first-page":"1140","volume":"1139","author":"Ranu B. C.","year":"1999","journal-title":"J. Chem. Soc., Perkin Trans. 1"},{"key":"ol034434lb00002\/ol034434lb00002_8","first-page":"4103","volume":"66","author":"Ranu B. C.","year":"2001","journal-title":"J. Org. Chem."},{"key":"ol034434lb00002\/ol034434lb00002_9","first-page":"5626","volume":"66","author":"Ranu B. C.","year":"2001","journal-title":"J. Org. Chem."},{"key":"ol034434lb00002\/ol034434lb00002_10","first-page":"5995","volume":"43","author":"Ranu B. C.","year":"2002","journal-title":"Tetrahedron Lett."},{"key":"ol034434lb00002\/ol034434lb00002_11","first-page":"4368","volume":"39","author":"Lim H. J.","year":"1998","journal-title":"Tetrahedron Lett."},{"key":"ol034434lb00002\/ol034434lb00002_12","first-page":"84","volume":"81","author":"Lee J. G.","year":"2001","journal-title":"Synthesis"},{"key":"ol034434lb00002\/ol034434lb00002_13","doi-asserted-by":"crossref","first-page":"3901","DOI":"10.1016\/S0040-4039(00)00512-8","volume":"41","author":"Chae H.","year":"2000","journal-title":"Tetrahedron Lett."},{"key":"ol034434lb00002\/ol034434lb00002_14","first-page":"2665","volume":"41","author":"Yadav J. S.","year":"2000","journal-title":"Tetrahedron Lett."},{"key":"ol034434lb00002\/ol034434lb00002_15","first-page":"1449","volume":"1447","author":"Yadav J. S.","year":"2000","journal-title":"Synlett"},{"key":"ol034434lb00002\/ol034434lb00002_16","first-page":"3938","volume":"40","author":"Reddy G. V.","year":"1999","journal-title":"Tetrahedron Lett."},{"key":"ol034434lb00002\/ol034434lb00002_17","first-page":"184","volume":"182","author":"Miyai T.","year":"1999","journal-title":"Synlett"},{"key":"ol034434lb00002\/ol034434lb00002_18","first-page":"8099","volume":"41","author":"Baek H. S.","year":"2000","journal-title":"Tetrahedron Lett."},{"key":"ol034434lb00003\/ol034434lb00003_1","doi-asserted-by":"crossref","first-page":"2318","DOI":"10.1016\/S0040-4039(03)00239-9","volume":"44","author":"Cardona F.","year":"2003","journal-title":"Tetrahedron Lett."},{"key":"ol034434lb00004\/ol034434lb00004_1","doi-asserted-by":"crossref","first-page":"1438","DOI":"10.1021\/cr940474e","volume":"98","author":"Bloch R.","year":"1998","journal-title":"Chem. Rev."},{"key":"ol034434lb00004\/ol034434lb00004_2","doi-asserted-by":"crossref","unstructured":"(b) Enders, D.; Reinhold:\u2009 U.Tetrahedron:\u2009 Asymmetry1997,8, 1895\u22121946.","DOI":"10.1016\/S0957-4166(97)00208-5"},{"key":"ol034434lb00004\/ol034434lb00004_3","first-page":"774","volume":"759","author":"Lombardo M.","year":"2000","journal-title":"Synthesis"},{"key":"ol034434lb00004\/ol034434lb00004_4","first-page":"454","volume":"442","author":"Merino P.","year":"2000","journal-title":"Synlett"},{"key":"ol034434lb00004\/ol034434lb00004_5","doi-asserted-by":"crossref","first-page":"713","DOI":"10.2174\/1385272023373987","volume":"6","author":"Lombardo M.","year":"2002","journal-title":"Curr. Org. Chem."},{"key":"ol034434lb00005\/ol034434lb00005_1","volume-title":"In 1,3-Dipolar Cycloaddition Chemistry","author":"Tufariello J. J.","year":"1984"},{"key":"ol034434lb00005\/ol034434lb00005_2","first-page":"173","volume":"36","author":"Confalone P. N.","year":"1988","journal-title":"Org. React."},{"key":"ol034434lb00005\/ol034434lb00005_3","volume-title":"VCH Publishers:\u2009 New York","author":"Torssell K. B. G.","year":"1988"},{"key":"ol034434lb00005\/ol034434lb00005_4","first-page":"425","volume":"53","author":"Frederickson M.","year":"1997","journal-title":"Tetrahedron"},{"key":"ol034434lb00006\/ol034434lb00006_1","first-page":"2558","volume":"101","author":"Huisgen R.","year":"1968","journal-title":"Chem. Ber."},{"key":"ol034434lb00006\/ol034434lb00006_2","first-page":"2567","volume":"101","author":"Huisgen R.","year":"1968","journal-title":"Chem. Ber."},{"key":"ol034434lb00006\/ol034434lb00006_3","first-page":"2584","volume":"101","author":"Huisgen R.","year":"1968","journal-title":"Chem. Ber."},{"key":"ol034434lb00006\/ol034434lb00006_4","first-page":"745","volume":"102","author":"Huisgen R.","year":"1969","journal-title":"Chem. Ber."},{"key":"ol034434lb00007\/ol034434lb00007_1","doi-asserted-by":"crossref","first-page":"3767","DOI":"10.1021\/ja01072a032","volume":"86","author":"LeBel N. A.","year":"1964","journal-title":"J. Am. Chem. Soc."},{"key":"ol034434lb00008\/ol034434lb00008_1","first-page":"5050","volume":"48","author":"Tice C. M.","year":"1983","journal-title":"J. Org. Chem."},{"key":"ol034434lb00009\/ol034434lb00009_1","doi-asserted-by":"crossref","first-page":"1688","DOI":"10.1021\/ja00344a063","volume":"105","author":"DeShong P.","year":"1983","journal-title":"J. Am. Chem. Soc."},{"key":"ol034434lb00010\/ol034434lb00010_1","doi-asserted-by":"crossref","first-page":"3453","DOI":"10.1016\/S0040-4020(01)96699-2","volume":"41","author":"Tufariello J. J.","year":"1985","journal-title":"Tetrahedron"},{"key":"ol034434lb00011\/ol034434lb00011_1","doi-asserted-by":"crossref","first-page":"3354","DOI":"10.1016\/S0040-4039(00)89062-0","volume":"31","author":"Cicchi S.","year":"1990","journal-title":"Tetrahedron Lett."},{"key":"ol034434lb00012\/ol034434lb00012_1","first-page":"1295","volume":"1289","author":"Dhavale D. D.","year":"1992","journal-title":"Liebigs Ann. Chem."},{"key":"ol034434lb00013\/ol034434lb00013_1","first-page":"1378","volume":"3","author":"Westermann B.","year":"2001","journal-title":"Org. Lett."},{"key":"ol034434lb00014\/ol034434lb00014_1","first-page":"2976","volume":"29","author":"Murahashi S.-I.","year":"1988","journal-title":"Tetrahedron Lett."},{"key":"ol034434lb00015\/ol034434lb00015_1","first-page":"6472","volume":"28","author":"Murahashi S.-I.","year":"1987","journal-title":"Tetrahedron Lett."},{"key":"ol034434lb00015\/ol034434lb00015_2","first-page":"2648","volume":"34","author":"Murahashi S.-I.","year":"1993","journal-title":"Tetrahedron Lett."},{"key":"ol034434lb00016\/ol034434lb00016_1","first-page":"4636","volume":"26","author":"Murahashi S.-I.","year":"1985","journal-title":"Tetrahedron Lett."},{"key":"ol034434lb00016\/ol034434lb00016_2","doi-asserted-by":"crossref","first-page":"2549","DOI":"10.1246\/bcsj.67.2542","volume":"67","author":"Kodera Y.","year":"1994","journal-title":"Bull. Chem. Soc. Jpn."},{"key":"ol034434lb00017\/ol034434lb00017_1","doi-asserted-by":"crossref","first-page":"3021","DOI":"10.1080\/00397910008087449","volume":"30","author":"Merino P.","year":"2000","journal-title":"Synth. Commun."},{"key":"ol034434lb00018\/ol034434lb00018_1","doi-asserted-by":"crossref","first-page":"1161","DOI":"10.1248\/cpb.29.1159","volume":"29","author":"Nose A.","year":"1981","journal-title":"Chem. Pharm. Bull."},{"key":"ol034434lb00019\/ol034434lb00019_1","unstructured":"General Procedure.The hydroxylamine (1 mmol) is dissolved into a 2:1 solution of EtOH and saturated aqueous NH4Cl (6 mL) in a 25-mL round-bottomed flask equipped with a Claisen condenser and a magnetic stirring bar. The appropriate amount of In powder (see Tables) is then added, and the mixture is heated under reflux. After completion of the reaction (TLC control), the mixture is cooled, filtered over Celite, and concentrated. Then, a saturated Na2CO3solution (15 mL) is added, and the product is extracted with ethyl acetate (3 \u00d7 15 mL). The organic phase is dried over anhydrous Na2SO4, filtered, and concentrated to afford the desired amine. When necessary, the amine has been purified by flash column chromatography."},{"key":"ol034434lb00020\/ol034434lb00020_1","first-page":"4370","volume":"40","author":"Baldwin J. E.","year":"1984","journal-title":"J. Tetrahedron"},{"key":"ol034434lb00021\/ol034434lb00021_1","volume-title":"for example, the following prices (Euros\/mol) of In and other commonly used reducing metals, extracted from the Aldrich 2003 catalogue:\u2009 In, 1332","author":"Compare"},{"key":"ol034434lb00022\/ol034434lb00022_1","first-page":"1738","volume":"65","author":"Araki S.","year":"1992","journal-title":"Bull. Chem. Soc. Jpn."},{"key":"ol034434lb00022\/ol034434lb00022_2","first-page":"9247","volume":"40","author":"Aug\u00e9 J.","year":"1999","journal-title":"Tetrahedron Lett."},{"key":"ol034434lb00022\/ol034434lb00022_3","doi-asserted-by":"crossref","first-page":"254","DOI":"10.1002\/1615-4169(20010330)343:3<251::AID-ADSC251>3.0.CO;2-8","volume":"343","author":"Steurer S.","year":"2001","journal-title":"Adv. Synth. Catal."},{"key":"ol034434lb00022\/ol034434lb00022_4","doi-asserted-by":"crossref","first-page":"2983","DOI":"10.1021\/ol016315g","volume":"3","author":"Lombardo M.","year":"2001","journal-title":"Org. Lett."},{"key":"ol034434lb00022\/ol034434lb00022_5","doi-asserted-by":"crossref","first-page":"128","DOI":"10.1039\/b110224a","volume":"4","author":"Gordon C. M.","year":"2002","journal-title":"Green Chem."}],"container-title":["Organic Letters"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/pubs.acs.org\/doi\/pdf\/10.1021\/ol034434l","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2021,9,22]],"date-time":"2021-09-22T02:49:10Z","timestamp":1632278950000},"score":1,"resource":{"primary":{"URL":"https:\/\/pubs.acs.org\/doi\/10.1021\/ol034434l"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2003,4,22]]},"references-count":55,"journal-issue":{"issue":"10","published-print":{"date-parts":[[2003,5,1]]}},"alternative-id":["10.1021\/ol034434l"],"URL":"https:\/\/doi.org\/10.1021\/ol034434l","relation":{},"ISSN":["1523-7060","1523-7052"],"issn-type":[{"value":"1523-7060","type":"print"},{"value":"1523-7052","type":"electronic"}],"subject":[],"published":{"date-parts":[[2003,4,22]]}}}