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Angew Chem Int Ed Engl. 2016 Apr 25;55(18):5446-51. doi: 10.1002/anie.201600596. Epub 2016 Mar 23.

Organophotocatalysis: Insights into the Mechanistic Aspects of Thiourea-Mediated Intermolecular [2+2] Photocycloadditions.

Author information

1
Department of Chemistry and Biochemistry, North Dakota State University, Fargo, ND, 58108-6050, USA.
2
Department of Chemistry, Columbia University, New York, NY, 10025, USA.
3
Department of Chemistry and Biochemistry, North Dakota State University, Fargo, ND, 58108-6050, USA. mukund.sibi@ndsu.edu.
4
Department of Chemistry and Biochemistry, North Dakota State University, Fargo, ND, 58108-6050, USA. jayaraman.sivaguru@ndsu.edu.

Abstract

Mechanistic investigations of the intermolecular [2+2] photocycloaddition of coumarin with tetramethylethylene mediated by thiourea catalysts reveal that the reaction is enabled by a combination of minimized aggregation, enhanced intersystem crossing, and altered excited-state lifetime(s). These results clarify how the excited-state reactivity can be manipulated through catalyst-substrate interactions and reveal a third mechanistic pathway for thiourea-mediated organo-photocatalysis.

KEYWORDS:

asymmetric catalysis; organocatalysis; photochemistry; photocycloadditions; thioureas

PMID:
27005562
DOI:
10.1002/anie.201600596
[Indexed for MEDLINE]

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