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Iron-Catalyzed Functionalization of Alcohols and Alkenes: Forging Carbon-Heteroatom Bonds with Earth Abundant Metals
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| 자료유형 | 학위논문 |
|---|---|
| 서명/저자사항 | Iron-Catalyzed Functionalization of Alcohols and Alkenes: Forging Carbon-Heteroatom Bonds with Earth Abundant Metals. |
| 개인저자 | Marcyk, Paul Tomas. |
| 단체저자명 | Indiana University. Chemistry. |
| 발행사항 | [S.l.]: Indiana University., 2019. |
| 발행사항 | Ann Arbor: ProQuest Dissertations & Theses, 2019. |
| 형태사항 | 459 p. |
| 기본자료 저록 | Dissertations Abstracts International 81-03B. Dissertation Abstract International |
| ISBN | 9781085742146 |
| 학위논문주기 | Thesis (Ph.D.)--Indiana University, 2019. |
| 일반주기 |
Source: Dissertations Abstracts International, Volume: 81-03, Section: B.
Advisor: Cook, Silas . |
| 이용제한사항 | This item must not be sold to any third party vendors.This item must not be added to any third party search indexes. |
| 요약 | 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. |
| 일반주제명 | Organic chemistry. Chemistry. |
| 언어 | 영어 |
| 바로가기 | 
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