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020 ▼a 9781085742146
035 ▼a (MiAaPQ)AAI22584918
040 ▼a MiAaPQ ▼c MiAaPQ ▼d 247004
0820 ▼a 540
1001 ▼a Marcyk, Paul Tomas.
24510 ▼a Iron-Catalyzed Functionalization of Alcohols and Alkenes: Forging Carbon-Heteroatom Bonds with Earth Abundant Metals.
260 ▼a [S.l.]: ▼b Indiana University., ▼c 2019.
260 1 ▼a Ann Arbor: ▼b ProQuest Dissertations & Theses, ▼c 2019.
300 ▼a 459 p.
500 ▼a Source: Dissertations Abstracts International, Volume: 81-03, Section: B.
500 ▼a Advisor: Cook, Silas .
5021 ▼a Thesis (Ph.D.)--Indiana University, 2019.
506 ▼a This item must not be sold to any third party vendors.
506 ▼a This item must not be added to any third party search indexes.
520 ▼a An efficient iron Lewis acid catalyst for the activation of alcohol and alkenes has been developed. Using abundant starting materials, unactivated alcohols are directly substituted with sulfonamide nucleophiles to form carbon-nitrogen bonds. By tethering the nucleophile to the electrophile in an intramolecular variant, a stereospecific mechanism is operative, transferring chiral information from secondary and even tertiary alcohols. In a related series of reactions, the same iron catalyst can be used to promote the hydrofunctionalization of unactivated alkenes. This system uses sulfonamides, primary and secondary alcohols, and select thiols to rapidly form carbon-nitrogen, carbon-oxygen, and carbon-sulfur bonds from simple alkene building blocks. Finally, these two paradigms are unified in an iron-catalyzed annulation reaction for the synthesis of tetrahydroisoquinolines. Starting from a benzylic alcohol and an unactivated alkene, the tandem iron-catalyzed alcohol substitution and hydroamination with a sulfonamide nucleophile, forms a biologically relevant six membered heterocyclic scaffold in a single synthetic step.
590 ▼a School code: 0093.
650 4 ▼a Organic chemistry.
650 4 ▼a Chemistry.
690 ▼a 0490
690 ▼a 0485
71020 ▼a Indiana University. ▼b Chemistry.
7730 ▼t Dissertations Abstracts International ▼g 81-03B.
773 ▼t Dissertation Abstract International
790 ▼a 0093
791 ▼a Ph.D.
792 ▼a 2019
793 ▼a English
85640 ▼u http://www.riss.kr/pdu/ddodLink.do?id=T15492893 ▼n KERIS ▼z 이 자료의 원문은 한국교육학술정보원에서 제공합니다.
980 ▼a 202002 ▼f 2020
990 ▼a ***1008102
991 ▼a E-BOOK