A Mitsunobu reaction to functionalized cyclic and bicyclic N-arylamines |
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| Authors: | Daniel M Gill Matthew Iveson Ian Collins Alan M Jones |
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| Institution: | 1. School of Pharmacy, University of Birmingham, Edgbaston B15 2TT, UK;2. School of Chemistry, University of Birmingham, Edgbaston B15 2TT, UK;3. Division of Chemistry and Environmental Science, Manchester Metropolitan University, M1 5GD, UK;4. Cancer Research UK Cancer Therapeutics Unit, The Institute of Cancer Research, London SM2 5NG, UK |
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| Abstract: | The scope of an unexpected Mitsunobu cyclisation to prepare N-arylated Fsp3-enriched azacycles was investigated. In the current study, we have identified whether a pKa-dependent Mitsunobu cyclodehydration or a pKa-independent Mitsunobu intramolecular reaction was in operation. A Mitsunobu reaction, creating a leaving group, followed by intramolecular nucleophilic displacement was determined to be the dominant pathway. |
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| Keywords: | Mitsunobu Cyclodehydration Nucleophilic aromatic substitution Intramolecular Cyclisation |
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