1-Isobutyl-7-methoxy-2,3,4,9-tetrahydro-1H-beta-carboline
CAS Number:
175975-76-5
Molecular Formula:
C16H22N2O
Photo-hydroacylation: 1-tetralones from ortho-allylbenzaldehydes
Literature Information
Publication Date
2023-10-10
DOI
10.1039/D3QO01510F
Impact Factor
5.281
Authors
Veronika Schmalz, Ulrich Koert
View Original
Abstract
A light-induced intramolecular hydroacylation of ortho-allylbenzaldehydes is presented, yielding the selective formation of a six-membered ring in 1-tetralones. The photo-hydroacylation proceeds at 365 nm, ambient temperature, and additive-free conditions. The proposed mechanistic pathway involves a light-induced 1,5-hydrogen atom transfer (1,5-HAT) and a radical recombination process leading to the formation of the 1-tetralone product. Deuteration and radical-clock experiments support the mechanism. This efficient photo-hydroacylation provides a valuable method for the synthesis of various tetralone scaffolds through light activation.
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Source Journal
Organic Chemistry Frontiers
CiteScore:
7.8
Self-citation Rate:
8.7%
Articles per Year:
724
Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry
Recommended Compounds
Benzyl 6-oxo-3,6-dihydro-1(2H)-pyridinecarboxylate
CAS Number:
725746-35-0
Molecular Formula:
C13H13NO3
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