A weak carbonyl coordination-guided regioselective C4 allylation of indoles is demonstrated using the versatile Morita-Baylis-Hillman adduct in the presence of Rh catalysts in a redox-neutral fashion. The substrate scope, functional group diversity, oxidant free character, mechanistic aspects, and synthetic utilities are important practical features.
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http://dx.doi.org/10.1021/acs.orglett.9b03823 | DOI Listing |
Chem Asian J
May 2023
Department of Chemistry, Indian Institute of Technology Madras, Chennai, 600036, India.
A weak coordination guided Ru(II)-catalyzed oxidative functionalization of arenes with unactivated olefins is developed, offering a wide variety of ortho-alkenylated benzamides, acetophenones, and benzophenone in high yields. The protocol accommodates several bioactive molecules and allows downstream synthetic manipulations leading to a 2,3-benzodiazepine scaffold. The reaction features a reversible metalation step and favors a regioselective β-hydride elimination event.
View Article and Find Full Text PDFOrg Lett
December 2019
Department of Chemistry , Indian Institute of Technology Guwahati, Guwahati 781039 , India.
A weak carbonyl coordination-guided regioselective C4 allylation of indoles is demonstrated using the versatile Morita-Baylis-Hillman adduct in the presence of Rh catalysts in a redox-neutral fashion. The substrate scope, functional group diversity, oxidant free character, mechanistic aspects, and synthetic utilities are important practical features.
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