{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,1,17]],"date-time":"2026-01-17T21:03:41Z","timestamp":1768683821529,"version":"3.49.0"},"reference-count":63,"publisher":"Wiley","issue":"36","license":[{"start":{"date-parts":[[2011,7,18]],"date-time":"2011-07-18T00:00:00Z","timestamp":1310947200000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Angew Chem Int Ed"],"published-print":{"date-parts":[[2011,8,29]]},"DOI":"10.1002\/anie.201103700","type":"journal-article","created":{"date-parts":[[2011,7,18]],"date-time":"2011-07-18T13:42:53Z","timestamp":1310996573000},"page":"8325-8328","source":"Crossref","is-referenced-by-count":78,"title":["Titanium\u2010Mediated Amination of Grignard Reagents Using Primary and Secondary Amines"],"prefix":"10.1002","volume":"50","author":[{"given":"Timothy J.","family":"Barker","sequence":"first","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Elizabeth R.","family":"Jarvo","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"311","published-online":{"date-parts":[[2011,7,18]]},"reference":[{"key":"e_1_2_3_1_2","unstructured":"For reviews see:"},{"key":"e_1_2_3_2_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200300594"},{"key":"e_1_2_3_2_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200300594"},{"key":"e_1_2_3_3_2","doi-asserted-by":"publisher","DOI":"10.1021\/ar9600650"},{"key":"e_1_2_3_4_2","doi-asserted-by":"publisher","DOI":"10.1002\/(SICI)1521-3757(19980803)110:15<2154::AID-ANGE2154>3.0.CO;2-C"},{"key":"e_1_2_3_4_3","doi-asserted-by":"publisher","DOI":"10.1002\/(SICI)1521-3773(19980817)37:15<2046::AID-ANIE2046>3.0.CO;2-L"},{"key":"e_1_2_3_5_2","doi-asserted-by":"publisher","DOI":"10.1007\/3-540-45313-X_5"},{"key":"e_1_2_3_6_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo020297e"},{"key":"e_1_2_3_7_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.ccr.2004.09.014"},{"key":"e_1_2_3_8_2","unstructured":"For reviews see:"},{"key":"e_1_2_3_9_2","first-page":"906","volume":"5","author":"Watson I. D. G.","year":"2002","journal-title":"Curr. Opin. Drug Discovery Dev."},{"key":"e_1_2_3_10_2","doi-asserted-by":"publisher","DOI":"10.1002\/(SICI)1521-3765(20000417)6:8<1281::AID-CHEM1281>3.0.CO;2-F"},{"key":"e_1_2_3_11_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr00098a014"},{"key":"e_1_2_3_12_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol035629w"},{"key":"e_1_2_3_13_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo00126a062"},{"key":"e_1_2_3_14_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo981412h"},{"key":"e_1_2_3_15_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200353241"},{"key":"e_1_2_3_15_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200353241"},{"key":"e_1_2_3_16_2","unstructured":"Copper\u2010catalyzed amination using hydroxylamines:"},{"key":"e_1_2_3_17_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja049474e"},{"key":"e_1_2_3_18_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo048168g"},{"key":"e_1_2_3_19_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo051999h"},{"key":"e_1_2_3_20_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol0702829"},{"key":"e_1_2_3_21_2","first-page":"1799","author":"Berman A. M.","year":"2005","journal-title":"Synlett"},{"key":"e_1_2_3_22_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja202563w"},{"key":"e_1_2_3_23_2","unstructured":"\u00a0"},{"key":"e_1_2_3_24_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200801427"},{"key":"e_1_2_3_24_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200801427"},{"key":"e_1_2_3_25_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja101939r"},{"key":"e_1_2_3_26_2","unstructured":"Whereas primaryN\u2010chloramines are unstable the corresponding hydroxylamine derivatives are isolable and undergo copper\u2010catalyzed cross\u2010coupling. See Ref\u2005[3]."},{"key":"e_1_2_3_27_2","unstructured":"Representative examples are shown in Table\u20051. See the Supporting Information for more detail. Using modified procedures of methods reported in Ref.\u2005[5b] and [5c] provided unsatisfactory yields of the desired product."},{"key":"e_1_2_3_28_2","unstructured":"Nucleophilic aryltitanium intermediates undergo addition to aldehydes and ketones. Selected examples of enantioselective titanium\u2010catalyzed addition of arylboronic acids to aldehydes and ketones:"},{"key":"e_1_2_3_29_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol902454n"},{"key":"e_1_2_3_30_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr040698p"},{"key":"e_1_2_3_31_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol0352963"},{"key":"e_1_2_3_32_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4020(01)90475-2"},{"key":"e_1_2_3_33_2","unstructured":"For titanium\u2010catalyzed hydroamination:"},{"key":"e_1_2_3_34_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr0306788"},{"key":"e_1_2_3_35_2","doi-asserted-by":"publisher","DOI":"10.1039\/b600981f"},{"key":"e_1_2_3_36_2","doi-asserted-by":"publisher","DOI":"10.1055\/s-2004-829579"},{"key":"e_1_2_3_37_2","first-page":"2243","author":"Lee A. V.","year":"2007","journal-title":"Eur. J. Inorg. Chem."},{"key":"e_1_2_3_38_2","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.200701146"},{"key":"e_1_2_3_39_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja0628811"},{"key":"e_1_2_3_40_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo991864"},{"key":"e_1_2_3_41_2","unstructured":"See the Supporting Information for details."},{"key":"e_1_2_3_42_2","unstructured":"See the Supporting Information for details."},{"key":"e_1_2_3_43_2","doi-asserted-by":"publisher","DOI":"10.1055\/s-1985-31450"},{"key":"e_1_2_3_44_2","unstructured":"Biaryl piperazines have been shown to be effective in the treatment of:"},{"key":"e_1_2_3_45_2","doi-asserted-by":"publisher","DOI":"10.1021\/jm980274l"},{"key":"e_1_2_3_46_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.bmcl.2003.11.035"},{"key":"e_1_2_3_47_2","doi-asserted-by":"publisher","DOI":"10.1021\/jm101163m"},{"key":"e_1_2_3_48_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.bmcl.2005.09.020"},{"key":"e_1_2_3_49_2","unstructured":"For the synthesis of anilines1\u20134and6 the Grignard reagents were prepared using the conventional method from the aryl bromide and Mg turnings. The Grignard reagents used for the synthesis of anilines5 7 and8were prepared using Mg\u2013Br exchange. The Grignard reagent used for the synthesis of aniline9was prepared using Mg\u2013I exchange;"},{"key":"e_1_2_3_50_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200454084"},{"key":"e_1_2_3_50_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200454084"},{"key":"e_1_2_3_51_2","doi-asserted-by":"publisher","DOI":"10.1002\/(SICI)1521-3757(19980619)110:12<1801::AID-ANGE1801>3.0.CO;2-R"},{"key":"e_1_2_3_51_3","doi-asserted-by":"publisher","DOI":"10.1002\/(SICI)1521-3773(19980703)37:12<1701::AID-ANIE1701>3.0.CO;2-U"},{"key":"e_1_2_3_52_2","unstructured":"Use of 3\u2010pyridylmagnesium bromide in the titanium\u2010mediated reaction withN\u2010dibutyl\u2010N\u2010chloroamine resulted in 20\u2009% yield of the desired product. The 2\u2010pyridylmagnesium bromide and 4\u2010pyridylmagnesium bromide did not afford any desired product under the reaction conditions."},{"key":"e_1_2_3_53_2","unstructured":"Androgen receptor modulators could provide effective treatments against diseases common among aging males with low androgen levels for example prostate cancer:"},{"key":"e_1_2_3_54_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0094-0143(02)00084-8"},{"key":"e_1_2_3_55_2","first-page":"3068","volume":"55","author":"Hobisch A.","year":"1995","journal-title":"Cancer Res."},{"key":"e_1_2_3_56_2","doi-asserted-by":"publisher","DOI":"10.1038\/nm972"},{"key":"e_1_2_3_57_2","doi-asserted-by":"publisher","DOI":"10.1021\/cc060096e"}],"container-title":["Angewandte Chemie International Edition"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.wiley.com\/onlinelibrary\/tdm\/v1\/articles\/10.1002%2Fanie.201103700","content-type":"unspecified","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/anie.201103700","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2023,10,16]],"date-time":"2023-10-16T09:23:01Z","timestamp":1697448181000},"score":1,"resource":{"primary":{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/10.1002\/anie.201103700"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2011,7,18]]},"references-count":63,"journal-issue":{"issue":"36","published-print":{"date-parts":[[2011,8,29]]}},"alternative-id":["10.1002\/anie.201103700"],"URL":"https:\/\/doi.org\/10.1002\/anie.201103700","archive":["Portico"],"relation":{},"ISSN":["1433-7851","1521-3773"],"issn-type":[{"value":"1433-7851","type":"print"},{"value":"1521-3773","type":"electronic"}],"subject":[],"published":{"date-parts":[[2011,7,18]]}}}