and Fuels Changzhi Li,† Xiaochen Zhao,† Aiqin Wang,† George W. Huber,†,‡ and Tao Zhang*,† †State Key Laborotary of Catalysis, iChEM (Collaborative Innovation Center of Chemistry for Energy Materials), Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian 116023, China ‡Department of Chemical and Biological Engineering, University of WisconsinMadison, Madison, Wisconsin 53706, United States

Catalytic Transformation of Lignin for the Production of Chemicals and Fuels

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Advances in transition metal (Pd, Ni, Fe)-catalyzed cross-coupling reactions using alkyl-organometallics as reaction partners.

Over the last decade, substantial research has led to the introduction of an impressive number of efficient procedures which allow the selective construction of CC bonds by directly connecting two different CH bonds under oxidative conditions. Common to these methodologies is the generation of the reactive intermediates in situ by activation of both CH bonds. This strategy was introduced by the group of Li as cross-dehydrogenative coupling (CDC) and discloses waste-minimized synthetic alternatives to classic coupling procedures which rely on the use of prefunctionalized starting materials. This Review highlights the recent progress in the field of cross-dehydrogenative C sp 3C formations and provides a comprehensive overview on existing procedures and employed methodologies.

The Cross-Dehydrogenative Coupling of C sp 3H Bonds: A Versatile Strategy for CC Bond Formations

Transition-Metal-Catalyzed C−S, C−Se, and C−Te Bond Formation via Cross-Coupling and Atom-Economic Addition Reactions

140 years ago Adolf von Baeyer proposed the structure of a heteroaromatic compound which revolutionized organic and medical chemistry: indole. After more than a century, indole itself and the complexity of naturally occurring indole derivatives continue to inspire and influence developments in synthetic chemistry. In particular, the ubiquitous presence of indole rings in pharmaceuticals, agrochemicals, and functional materials are testament to the ever increasing interest in the design of mild and efficient synthetic routes to functionalized indole derivatives. This Review emphasizes the achievements in the selective catalytic functionalization of indoles (C-C bond-forming processes) over the last four years.

Catalytic Functionalization of Indoles in a New Dimension

Nickel-induced conversion of carbon-oxygen into carbon-carbon bonds. One-step transformations of enol ethers into olefins and aryl ethers into biaryls

Etude de la substitution de groupes alcoxy d'enols ethers (methoxy-1 cyclohexenes, methoxy-1 alcenes-1, benzofuranne, dihydro-2,3 furanne) et de (methyl aryl) ethers par l'intermediaire de la reaction de Grignard catalysee par le dichlorure de bis-triphenylphosphine-nickel

Transformation of carbon-oxygen into carbon-carbon bonds mediated by low-valent nickel species

The reactions of alkenyl sulphides, benzenethiols, and aryl sulphides with methylmagnesium and arylmagnesium bromides, mediated by bis(triphenylphosphine)nickel dichloride, in benzene solution have been shown to lead to olefins (predominantly with retention of configuration), toluenes, and biphenyls in medium to high yields.

Nickel-induced conversion of carbon–sulphur into carbon–carbon bonds. One-step transformations of enol sulphides into olefins and benzenethiol derivatives into alkylarenes and biaryls

Enrique L. Michelotti

Papers

Nickel-induced conversion of carbon-oxygen into carbon-carbon bonds. One-step transformations of enol ethers into olefins and aryl ethers into biaryls

Transformation of carbon-oxygen into carbon-carbon bonds mediated by low-valent nickel species

Nickel-induced conversion of carbon–sulphur into carbon–carbon bonds. One-step transformations of enol sulphides into olefins and benzenethiol derivatives into alkylarenes and biaryls

Replacement of methylthio functions on aromatic heterocycles by hydrogen, alkyl and aryl groups via nickel-induced Grignard reactions

Synthesis of prenylated indoles