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However, the yields of the <jats:italic>N<\/jats:italic>\u2010<jats:sup>11<\/jats:sup>C\u2010methylated compounds are often insufficient. In this study, we developed an efficient method for base\u2010free reductive <jats:italic>N<\/jats:italic>\u2010<jats:sup>11<\/jats:sup>C\u2010methylation that is applicable to a wide variety of substrates, including arylamines bearing electron\u2010withdrawing and electron\u2010donating substituents. A 2\u2010picoline borane complex, which is a stable and mild reductant, was used. Dimethyl sulfoxide was used as the primary reaction solvent, and glacial acetic acid or aqueous acetic acid was used as a cosolvent. While reductive <jats:italic>N<\/jats:italic>\u2010<jats:sup>11<\/jats:sup>C\u2010methylation efficiently proceeded under anhydrous conditions in most cases, the addition of water to the reductive <jats:italic>N<\/jats:italic>\u2010<jats:sup>11<\/jats:sup>C\u2010methylation generally increased the yield of the <jats:italic>N<\/jats:italic>\u2010<jats:sup>11<\/jats:sup>C\u2010methylated compounds. Substrates with hydroxy, carboxyl, nitrile, nitro, ester, amide, and phenone moieties and amine salts were applicable to the reaction. This proposed method for reductive <jats:italic>N<\/jats:italic>\u2010<jats:sup>11<\/jats:sup>C\u2010methylation should be applicable to a wide variety of substrates, including thermo\u2010labile and base\u2010sensitive compounds because the reaction was performed under relatively mild conditions (70\u00b0C) without the need for a base.<\/jats:p>","DOI":"10.1002\/jlcr.4095","type":"journal-article","created":{"date-parts":[[2024,5,4]],"date-time":"2024-05-04T06:09:54Z","timestamp":1714802994000},"page":"254-262","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":1,"title":["Efficient Reductive <i>N<\/i>\u2010<sup>11<\/sup>C\u2010Methylation Using Arylamines or Alkylamines and In\u00a0Situ\u2013Generated [<sup>11<\/sup>C]Formaldehyde From [<sup>11<\/sup>C]Methyl Iodide"],"prefix":"10.1002","volume":"67","author":[{"ORCID":"https:\/\/orcid.org\/0000-0003-2966-3126","authenticated-orcid":false,"given":"Tatsuya","family":"Kikuchi","sequence":"first","affiliation":[{"name":"Department of Advanced Nuclear Medicine Sciences, Institute for Quantum Medical Science National Institutes for Quantum Science and Technology  Chiba Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-7117-6917","authenticated-orcid":false,"given":"Toshimitsu","family":"Okamura","sequence":"additional","affiliation":[{"name":"Department of Advanced Nuclear Medicine Sciences, Institute for Quantum Medical Science National Institutes for Quantum Science and Technology  Chiba Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Ming\u2010Rong","family":"Zhang","sequence":"additional","affiliation":[{"name":"Department of Advanced Nuclear Medicine Sciences, Institute for Quantum Medical Science National Institutes for Quantum Science and Technology  Chiba Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2024,5,4]]},"reference":[{"key":"e_1_2_8_2_1","doi-asserted-by":"publisher","DOI":"10.1016\/0969\u20108051(94)00083\u2010v"},{"key":"e_1_2_8_3_1","doi-asserted-by":"publisher","DOI":"10.1002\/jlcr.854"},{"key":"e_1_2_8_4_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.apradiso.2004.09.003"},{"key":"e_1_2_8_5_1","doi-asserted-by":"publisher","DOI":"10.1021\/jm700970s"},{"key":"e_1_2_8_6_1","doi-asserted-by":"publisher","DOI":"10.1021\/jm901057p"},{"key":"e_1_2_8_7_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bmc.2010.10.018"},{"key":"e_1_2_8_8_1","doi-asserted-by":"publisher","DOI":"10.1021\/ml500413d"},{"key":"e_1_2_8_9_1","doi-asserted-by":"publisher","DOI":"10.1021\/acsmedchemlett.0c00127"},{"key":"e_1_2_8_10_1","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.201101499"},{"key":"e_1_2_8_11_1","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.201500924"},{"key":"e_1_2_8_12_1","doi-asserted-by":"publisher","DOI":"10.1186\/s41181\u2010019\u20100065\u20104"},{"issue":"5","key":"e_1_2_8_13_1","first-page":"425","article-title":"A General Method for Labeling Proteins With 11C","volume":"16","author":"Straatmann M. 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