Decarboxylative reactions with and without light – a comparison

This chapter highlights recent developments in phenol dearomatization using organoiodane reagents and a selection of applications in natural product synthesis.

Phenol Dearomatization with Hypervalent Iodine Reagents.

The copper(II)-promoted free-radical oxidative difunctionalization of terminal alkenes to access ketoazides by utilizing molecular oxygen has been reported. A series of styrene derivatives have been evaluated and were found to be compatible to give the desired difunctionalized products in moderate to good yields. The role of molecular oxygen both as an oxidant and oxygen atom source in this catalytic transformation has been unquestionably demonstrated by 18O-labeling studies and a radical mechanistic pathway involving the oxidative formation of azidyl radicals is also designed. This environment-friendly catalytic oxidative protocol can transform aldehyde to nitrile.

Copper-Catalyzed Oxidative Difunctionalization of Terminal Unactivated Alkenes.

Reduction of N,N-Dimethylcarboxamides to Aldehydes by Sodium Hydride–Iodide Composite

One-Pot Synthesis of Deuterated Aldehydes from Arylmethyl Halides

Triphenylphosphine/Triethylamine‐Mediated Decarboxylation of α‐Oxocarboxylic Acids and Application in a One‐Pot Synthesis of Deuterated Aldehydes.

Diels–Alder Reactions of Masked o‐Benzoquinones with 1‐Vinylcyclohexenes: A Short and Efficient Entry to Highly Functionalized Decahydrophenanthrene Skeleton

Masked o-benzoquinones generated in situ from o-methoxyphenols and methanol undergo Diels—Alder reaction with 1-vinylcyclohexenes to provide decahydrophenanthrenes along with bicyclo[2.2.2]octenone derivatives.

Diels—Alder Reactions of Masked o-Benzoquinones with 1-Vinylcyclohexenes: A Short and Efficient Entry to Highly Functionalized Decahydrophenanthrene Skeleton.

A broad range of functionalized aryl α-oxocarboxylic acids as well as hetaryl and alkyl substituted analogues serve as effective synthons for aldehydes which may be isolated in moderate to high yields.

Guang-Hao Niu

Papers

Triphenylphosphine/Triethylamine‐Mediated Decarboxylation of α‐Oxocarboxylic Acids and Application in a One‐Pot Synthesis of Deuterated Aldehydes.

Diels–Alder Reactions of Masked o‐Benzoquinones with 1‐Vinylcyclohexenes: A Short and Efficient Entry to Highly Functionalized Decahydrophenanthrene Skeleton

Diels—Alder Reactions of Masked o-Benzoquinones with 1-Vinylcyclohexenes: A Short and Efficient Entry to Highly Functionalized Decahydrophenanthrene Skeleton.

Triphenylphosphine/Triethylamine-Mediated Decarboxylation of α-Oxocarboxylic Acids and Application in a One-Pot Synthesis of Deuterated Aldehydes.