Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 58, Issue 47, Pages 16878-16883Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201910641
Keywords
dihydropyridines; Minisci reaction; photochemistry; radical chemistry; synthetic methods
Categories
Funding
- MICIU [CTQ2016-75520-P]
- AGAUR [2017 SGR 981]
- European Research Council [ERC-2015-CoG 681840 - CATA-LUX]
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We report herein a visible light-mediated C-H hydroxyalkylation of quinolines and isoquinolines that proceeds via a radical path. The process exploits the excited-state reactivity of 4-acyl-1,4-dihydropyridines, which can readily generate acyl radicals upon blue light absorption. By avoiding the need for external oxidants, this radical-generating strategy enables a departure from the classical, oxidative Minisci-type pattern and unlocks a unique reactivity, leading to hydroxyalkylated heteroarenes. Mechanistic investigations provide evidence that a radical-mediated spin-center shift is the key step of the process. The method's mild reaction conditions and high functional group tolerance accounted for the late-stage functionalization of active pharmaceutical ingredients and natural products.
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