The Vinyl Moiety as a Handle for Regiocontrol in the Preparation of Unsymmetrical 2,3‐Aliphatic‐Substituted Indoles and Pyrroles

Abstract

Rho‐Rho‐Rho your boat: A rhodium catalyst effects the regioselective oxidative coupling of enynes with N‐aryl ureas (X=NR2) and N‐vinylacetamides (X=C(O)Me), affording the corresponding 2‐alkenylindoles and 2‐alkenylpyrroles in good yield. Simple hydrogenation delivers the C2/C3‐aliphatic‐substituted indole or pyrrole (see scheme).

Pyridine synthesis from oximes and alkynesviarhodium(iii) catalysis: Cp* and Cptprovide complementary selectivity

“…8 This method affords access to a variety of nitrogen containing heterocycles including indoles, 9 pyrroles, 10 isoquinolines, 11 and dihydro-isoquinolones. 12 We envisioned that pyridines could be accessed from α,β-unsaturated oximes 13 and alkynes, with the N–O bond of the oxime acting as an internal oxidant.…”

Solvent‐Free Ruthenium(II)‐Catalyzed C–H Activation: Synthesis of Alkenylarylpyrazole Derivatives

“…However, the oxidative alkenylation of heteroarenes is named the Moritani-Fujiwara reaction. [8,9] In this regard, different palladium [10][11][12][13] and rhodium catalysts [14][15][16] have already been used to promote the oxidative alkenylation of heteroarenes with a variety of directing groups, namely, imines, [17,18] amines, [19] and carboxylates. [20,21] Rutheniumcatalyst-directed arylation of unactivated C-H bonds with phenols was reported by Ackermann.…”

A Coupling of Benzamides and Donor/Acceptor Diazo Compounds To Form γ-Lactams via Rh(III)-Catalyzed C–H Activation

“…1 This concept has been extensively explored in the Rh(III) catalyzed synthesis of nitrogen containing heterocycles mediated by C–H activation. 2 A wide swath of unsaturated heterocycles can be accessed though coupling amides, amines, oximes, and anilines with alkynes to access isoquinolones, 3 pyridones, 3d,4 isoquinolines, 5 pyridines, 5g,6 indoles, 7 and pyrroles. 7b,8 …”