Divergent and Synergistic Photocatalysis: Hydro- and Oxoalkylation of Vinyl Arenes for the Stereoselective Synthesis of Cyclopentanols via a Formal [4+1]-Annulation of 1,3-Dicarbonyls

URN to cite this document:

urn:nbn:de:bvb:355-epub-546935 Copy

DOI to cite this document:

10.5283/epub.54693 Copy

Katta, Narenderreddy ; Zhao, Quan-Qing ; Mandal, Tirtha ; Reiser, Oliver

License: Creative Commons Attribution Non-commercial No Derivatives 4.0 PDF - Published Version (3MB)

Date of publication of this fulltext: 12 Sep 2023 15:56

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Details

Item type:	Article
Open Access Type:	Hybrid Open Acces
Journal or Publication Title:	ACS Catalysis
Publisher:	AMER CHEMICAL SOC
Place of Publication:	WASHINGTON
Volume:	12
Number of Issue or Book Chapter:	22
Page Range:	pp. 14398-14407
Date:	9 November 2022
Institutions:	Chemistry and Pharmacy > Institut für Organische Chemie > Lehrstuhl Prof. Dr. Oliver Reiser Chemistry and Pharmacy > Institut für Organische Chemie > Lehrstuhl Prof. Dr. Oliver Reiser
Identification Number:	Value Type 10.1021/acscatal.2c04736 DOI
Keywords:	LIGHT PHOTOREDOX CATALYSIS; FLUOROPHORES; DONOR; cyclopentanol process; cyclopentanols; divergent synthesis; enolate oxidation; photoredox catalysis; synergistic catalysis; visible-light-induced homolysis
Dewey Decimal Classification:	500 Science > 540 Chemistry & allied sciences
Status:	Published
Refereed:	Yes, this version has been refereed
Created at the University of Regensburg:	Yes
Item ID:	54693

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Abstract

The controllable divergent reactivity of 1,3-dicarbonyls is described, which enables the efficient hydro-and oxoalkylation of vinyl arenes. Both reaction pathways are initiated through the formation of polarity-reversed C-centered-radical intermediates at the active methylene center of 1,3-dicarbonyls via direct photocatalytic C-H bond transformations. The oxoalkylation of alkenes is achieved ...

Abstract

The controllable divergent reactivity of 1,3-dicarbonyls is described, which enables the efficient hydro-and oxoalkylation of vinyl arenes. Both reaction pathways are initiated through the formation of polarity-reversed C-centered-radical intermediates at the active methylene center of 1,3-dicarbonyls via direct photocatalytic C-H bond transformations. The oxoalkylation of alkenes is achieved under aerobic conditions via a Cu(II)-photomediated rebound mechanism, while the corresponding hydroalkylation becomes possible under a nitrogen atmosphere by the combination of 4CzIPN and a Bronsted base. The breadth of these divergent protocols is demonstrated in the late-stage modification of drugs and natural products and by the transformation of the products to a variety of heterocycles such as pyridines, pyrroles, or furans. Moreover, the two catalytic modes can be combined synergistically for the stereoselective construction of cyclopentanol derivatives in a formal [4+1]-annulation process.

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Metadata last modified: 20 Sep 2023 06:54

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