Shared posts

05 Oct 08:38

Strain-Promoted Oxidative Annulation of Arynes and Cyclooctynes with Benzamides: Palladium-Catalyzed C–H/N–H Activation for the Synthesis of N-Heterocycles

by Xianglong Peng, Weiguo Wang, Chao Jiang, Di Sun, Zhenghu Xu and Chen-Ho Tung

TOC Graphic

Organic Letters
DOI: 10.1021/ol5025426
07 May 14:23

Synthesis of Biaryls through Aromatic CH Bond Activation: A Review of Recent Developments

by Ibrar Hussain, Tripti Singh

Abstract

This review describes recent progress made in the rapidly developing field of C[BOND]H bond activation, in particular for syntheses of biaryls. The catalysts presented here provide convenient strategies for the direct arylation of arenes, via single or double C[BOND]H bond activation, leading to inter-, and intramolecular carbon-carbon bond formation. The literature from mid-2009 to December 2013 has been discussed.

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22 Dec 00:35

Free-Radical Cascade Alkylarylation of Alkenes with Simple Alkanes: Highly Efficient Access to Oxindoles via Selective (sp3)C–H and (sp2)C–H Bond Functionalization

by Zejiang Li, Ye Zhang, Lizhi Zhang and Zhong-Quan Liu
lemule

Free-Radical Cascade Alkylarylation of Alkenes with Simple Alkanes: Highly Efficient Access to Oxindoles via Selective (sp3)C–H and (sp2)C–H Bond Functionalization

TOC Graphic

Organic Letters
DOI: 10.1021/ol4032478
20 Nov 11:21

Gold versus Palladium: A Regioselective Cycloisomerization of Aromatic Enynes

by Jessy Aziz, Gilles Frison, Patrick Le Menez, Jean-Daniel Brion, Abdallah Hamze, Mouad Alami
lemule

substrate

Abstract

Aromatic enynes can be transformed into arylnaphthalenes or benzofulvenes depending on the reaction conditions. Under gold(I) catalysis, exclusive or major 6-endo-dig cyclization took place leading to arylnaphthalenes. However, a catalytic system based on palladium iodide/1,3-bis(diphenylphosphino)propane, in the presence of cesium carbonate as a base was necessary to furnish exclusively 5-exo-dig cyclization pattern, regardless of the electronic effects of the substituents. In the latter transformation, a mechanistic study (kinetic isotopic effect, density functional theory) involving a C[BOND]H activation is suggested for the exclusive formation of benzofulvenes.

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