The rhodium(III)-catalyzed direct allylation of indolines with allylic carbonates at room temperature is described. These transformations provide the facile and efficient construction of C7-allylated indolic scaffold.
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http://dx.doi.org/10.1021/jo502733q | DOI Listing |
Chem Commun (Camb)
September 2024
EaStCHEM School of Chemistry, University of Edinburgh David Brewster Road, Edinburgh, EH9 3FJ, UK.
Indolines are common motifs within pharamceuticals and natural products. Boron catalysis enables the chemoselective allylation of indoles to give allylic indolines in excellent diastereoselectivity. Mechanistic studies revealed formation of the allylic borane, allylation of the imine tautomer of the indole and B-N/B-H transborylation for catalytic turnover.
View Article and Find Full Text PDFJ Am Chem Soc
May 2024
Organisch-Chemisches Institut, Heidelberg University, Im Neuenheimer Feld 270, 69120 Heidelberg, Germany.
Herein, the development of a light-mediated synthesis of functionalized indolines and tetrahydroquinolines is reported. These structural motifs are considered as highly valuable targets, attributed to their widespread occurrence in pharmaceuticals and natural products. The gold-mediated approach offers a direct route to functionalized indolines in yields of up to 81% under mild photochemical conditions.
View Article and Find Full Text PDFChemistry
June 2024
School of chemical sciences, Indian Association for the Cultivation of Science, Jadavpur, 700032, Kolkata, India.
Cyclohepta[b]indoles, prevalent in natural products and pharmaceuticals, are conventionally accessed via metal or Lewis acid-mediated cycloadditions with prefunctionalized substrates. Our study introduces an innovative sequential catalytic assembly for synthesizing cyclohepta[b]indoles from readily available isatin derivatives. The process involves three catalytic sequences: ring-closing metathesis, catalytic hydrogenation, and acid-catalyzed ring expansion.
View Article and Find Full Text PDFBeilstein J Org Chem
December 2023
College of Chemistry & Chemical Engineering, Yangzhou University, Jiangsu, Yangzhou 225002, China.
A straightforward synthetic protocol for the efficient construction of diazepine-containing spiroindolines has been developed and proceeds through a by base-promoted annulation reaction of α-halogenated -acylhydrazones and isatin-derived MBH carbonates. The reaction mechanism of this formal [4 + 3] annulation includes the in situ generated allylic ylide, nucleophilic substitution, Michael additon, and elimination processes. Additionally, the similar reaction with α-halogenated -tosylhydrazones also afforded -tosyl-substituted spiro[indoline-3,5'-[1,2]diazepine] in satisfactory yields.
View Article and Find Full Text PDFOrg Lett
August 2023
College of Chemical Engineering, State Key Laboratory Breeding Base of Green Chemical Synthesis Technology, Zhejiang University of Technology, Chaowang Road 18#, Hangzhou, 310014, China.
Herein, we describe a nickel-catalyzed asymmetric dearomative aryl-difluoroallylation reaction of indoles with α-trifluoromethyl alkenes as an electrophilic coupling partner. The reaction proceeds via a cascade sequence involving dearomative Heck cyclization and reductive allylic defluorination. A series of -difluoroallyl substituted indolines are obtained in moderate to good yields (36-77% yield) with excellent enantioselectivity (up to 99% ee).
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