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. 2015 Apr 21;13(15):4367-73.
doi: 10.1039/c5ob00055f.

Palladium-catalyzed α-arylation of carbonyls in the de novo synthesis of aromatic heterocycles

Harish K Potukuchi  1 , Anatol P Spork, Timothy J Donohoe
Affiliations

Palladium-catalyzed α-arylation of carbonyls in the de novo synthesis of aromatic heterocycles

Harish K Potukuchi et al. Org Biomol Chem. .

Abstract

Aromatic heterocycles are a very well represented motif in natural products and have found various applications in chemistry and material science, as well as being commonly found in pharmaceutical agents. Thus, new and efficient routes towards this class of compound are always desirable, particularly if they expand the scope of chemical methodology or facilitate more effective pathways to complex substitution patterns. This perspective covers recent developments in the de novo synthesis of aromatic heterocycles via palladium-catalysed α-arylation reactions of carbonyls, which is itself a powerful transformation that has undergone significant development in recent years.

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Figures

Fig. 1
Fig. 1. A selection of phosphine ligands and palladium-precatalysts used in the α-arylation reaction.
Scheme 1
Scheme 1. Synthesis of 2-substituted indoles.
Scheme 2
Scheme 2. Indole synthesis using imine α-arylation.
Scheme 3
Scheme 3. Synthesis of indoles, isoindoles and pyrrolo[3,4-b]indoles.
Scheme 4
Scheme 4. Synthesis of benzofurans from benzyl ketones.
Scheme 5
Scheme 5. Synthesis of benzofurans and benzothiophenes.
Scheme 6
Scheme 6. One-pot synthesis of benzofurans.
Scheme 7
Scheme 7. Synthesis of isoquinolines via α-arylation.
Scheme 8
Scheme 8. Modular synthesis via in situ functionalization; yields reported for both steps. aElectrophile E+.
Scheme 9
Scheme 9. C-4 Aryl isoquinolines via a one-pot process.
Scheme 10
Scheme 10. Synthesis of berberine.
Scheme 11
Scheme 11. Synthesis of palmatine and dehydrocorydaline.
None
Harish K. Potukuchi
None
Anatol P. Spork
None
Timothy J. Donohoe
See this image and copyright information in PMC

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