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Hull, Kami Ickes, Andrew R 2017-03-01T17:01:51Z 2017-03-01T17:01:51Z 2019-03-02T10:15:18Z 2016-12-02 2016-12 Amines are a prominent functionality found throughout organic molecules, including pharmaceuticals, agrochemicals, organic materials, and organic dyes.1 However, incorporation of amines into organic frameworks in step and atom economical fashion remains a significant challenge to synthetic chemists.2–4 In chapter 1, the importance of a class of compounds, 1,2-diamines is reviewed. Herein, many marketed pharmaceuticals, potential therapeutics, and natural products bearing this motif of interest are discussed. Additionally, 1,2-diamines have been shown as ligands for catalysis. Due to this interest in the 1,2-diamine functionality, some current synthetic methods to access 1,2-diamines will be shown. Chapter 2 discusses the hypothesis that a Lewis basic functionality could coordinate to a metal center and allow a hydroamination reaction to occur. Hydroamination was seen as a beneficial strategy to synthesize 1,2-diamines as olefins and amines are reacted in an atom-economical fashion. Initial reaction discovery of the rhodium-catalyzed intermolecular hydroamination of N-allylimines will be shown as well as reaction development. It was found that modest to high yields and high diastereoselectivities were obtained to synthesize 1,2-diamines with this methodology. Further, reaction development of secondary and primary N-allylamines will be discussed. These substrates offer attractive methods toward synthesizing 1,2-diamines by being easy to access. When secondary N-allylamines are employed, good yield is obtained for the desired hydroamination reaction. Excitingly, primary N-allylamines were able to be used as substrates for this transformation. This substrate class offered the shortest reaction times and proved to be effective for a wide range of amine nucleophiles. Submission published under a 24 month embargo labeled 'Closed Access', the embargo will last until 2018-12-01 The student, Andrew Ickes, accepted the attached license on 2016-12-01 at 10:52. The student, Andrew Ickes, submitted this Thesis for approval on 2016-12-01 at 10:58. This Thesis was approved for publication on 2016-12-02 at 14:51. DSpace SAF Submission Ingestion Package generated from Vireo submission #10393 on 2017-02-28 at 14:42:43 Made available in DSpace on 2017-03-01T17:01:51Z (GMT). No. of bitstreams: 2 ICKES-THESIS-2016.pdf: 5660215 bytes, checksum: d2ae53c4c6948b1621cd14272d16554f (MD5) LICENSE.txt: 4209 bytes, checksum: d9742ae80e6ca57c78065ece08cc7b95 (MD5) Previous issue date: 2016-12-02 Embargo set by: Seth Robbins for item 98719 Lift date: 2019-03-01T17:02:22Z Reason: Author requested closed access (OA after 2yrs) in Vireo ETD system Embargo set by: Seth Robbins for item 98719 Lift date: 2019-03-01T17:03:32Z Reason: Author requested closed access (OA after 2yrs) in Vireo ETD system Embargo set by: Seth Robbins for item 98719 Lift date: 2019-03-01T17:05:02Z Reason: Author requested closed access (OA after 2yrs) in Vireo ETD system Embargo set by: Seth Robbins for item 98719 Lift date: 2019-03-01T17:06:55Z Reason: Author requested closed access (OA after 2yrs) in Vireo ETD system Limited Restriction Lifted for Item 98719 on 2019-03-02T10:15:18Z. application/pdf http://hdl.handle.net/2142/95603 en Copyright 2016 Andrew Ickes rhodium hydroamination intermolecular stereoselective chemoselective The development of a rhodium-catalyzed chemo- and stereoselective hydroamination for the synthesis of 1,2-diamines text text Chemistry Chemistry University of Illinois at Urbana-Champaign Thesis M.S.