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2 article(s) from Fasana, Andrea

Palladium-catalyzed dual C–H or N–H functionalization of unfunctionalized indole derivatives with alkenes and arenes

Gianluigi Broggini,
Egle M. Beccalli,
Andrea Fasana and
Silvia Gazzola

Beilstein J. Org. Chem. 2012, 8, 1730–1746, doi:10.3762/bjoc.8.198

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Graphical Abstract

Scheme 1: Typical catalytic cycle for Pd(II)-catalyzed alkenylation of indoles.

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Scheme 2: Application of Fujiwara’s reaction to electron-rich heterocycles.

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Scheme 3: Regioselective alkenylation of the unprotected indole.

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Scheme 4: Plausible mechanism of the selective indole alkenylation, adapted from [49].

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Scheme 5: Directing-group control in intermolecular indole alkenylation.

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Scheme 6: Direct C–H alkenylation of N-(2-pyridyl)sulfonylindole.

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Scheme 7: N-Prenylation of indoles with 2-methyl-2-butene.

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Scheme 8: Proposed mechanism of the N-indolyl prenylation.

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Scheme 9: Regioselective arylation of indoles by dual C–H functionalization.

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Scheme 10: Plausible mechanism of the selective indole arylation.

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Scheme 11: Chemoselective cyclization of N-allyl-1H-indole-2-carboxamide derivatives.

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Scheme 12: Intramolecular annulations of alkenylindoles.

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Scheme 13: A mechanistic probe for intramolecular annulations of alkenylindoles, adapted from Ferreira et al. [66]....

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Scheme 14: Asymmetric indole annulations catalyzed by chiral Pd(II) complexes.

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Scheme 15: Aerobic Pd(II)-catalyzed endo cyclization and subsequent amide cleavage/ester formation.

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Scheme 16: Synthesis of the pyrimido[3,4-a]indole skeleton by intramolecular C-2 alkenylation.

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Scheme 17: Synthesis of azepinoindoles by oxidative Heck cyclization.

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Scheme 18: Enantioselective synthesis of 4-vinyl-substituted tetrahydro-β-carbolines.

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Scheme 19: Pd-catalyzed endo-cyclization of 3-alkenylindoles for the construction of carbazoles.

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Scheme 20: Pd-catalyzed hydroamination of 2-indolyl allenamides.

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Scheme 21: Amidation reaction of 1-allyl-2-indolecarboxamides.

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Scheme 22: Intramolecular cyclization of N-benzoylindole.

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Scheme 23: Intramolecular alkenylation/carboxylation of alkenylindoles.

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Scheme 24: Intermolecular alkenylation/carboxylation of 2-substituted indoles.

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Scheme 25: Mechanistic investigation of the cyclization/carboxylation reaction.

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Scheme 26: Plausible catalytic cycle for the cyclization/carboxylation of alkenylindoles, adapted from Liu et ...

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Scheme 27: Intramolecular domino reactions of indolylallylamides through alkenylation/halogenation or alkenyla...

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Scheme 28: Proposed mechanism for the alkenylation/esterification process through iminium intermediates.

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Scheme 29: Cyclization of 3-indolylallylcarboxamides involving 1,2-migration of the acyl group from spiro-inte...

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Scheme 30: Domino reactions of 2-indolylallylcarboxamides involving N–H functionalization.

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Scheme 31: Cyclization/acyloxylation reaction of 3-alkenylindoles.

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Scheme 32: Doubly intramolecular C–H functionalization of a 2-indolylcarboxamide bearing two allylic groups.

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Review

Published 11 Oct 2012

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Access to pyrrolo-pyridines by gold-catalyzed hydroarylation of pyrroles tethered to terminal alkynes

Elena Borsini,
Gianluigi Broggini,
Andrea Fasana,
Chiara Baldassarri,
Angelo M. Manzo and
Alcide D. Perboni

Beilstein J. Org. Chem. 2011, 7, 1468–1474, doi:10.3762/bjoc.7.170

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Scheme 1: Pd-catalyzed cyclization of N-allyl-pyrrole-2-carboxamides.

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Figure 1: Significant relationships among hydrogen and carbon atoms arising from 2D-NMR studies to determine ...

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Scheme 2: Proposed mechanism for the formation of the six-membered products.

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Full Research Paper

Published 26 Oct 2011

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