0000000000042964
AUTHOR
Guenther Lahm
showing 10 related works from this author
Unique regioselectivity in the C(sp3)-H α-alkylation of amines: the benzoxazole moiety as a removable directing group.
2014
The benzoxazol-2-yl- substituent was found to act as a removable activating and directing group in the Ir-catalyzed alkylation of C(sp(3))-H bonds adjacent to nitrogen in secondary amines. It can be easily introduced by oxidative coupling or by an SNAr reaction, and it can be removed by hydroxide or by hydride reduction. For 1,2,3,4-tetrahydroisoquinolines, activation exclusively takes place in the 3-position. A variety of activated as well as unactivated terminal olefins are suitable reaction partners.
ChemInform Abstract: Selective C-H Activation of Methoxy Groups in a Three-Component Photoreaction.
2016
Surprisingly, the photocatalytic activation of ethers by H-abstraction and addition of the generated radicals to iminium ions formed in situ from aldehydes and anilines predominantly yielded the products of methoxy activation for dimethoxymethane and 1,2-dimethoxyethane. Various anilines and aromatic as well as aliphatic aldehydes are suitable reaction partners for this three-component photoreaction (Porta-type process) which also provides a simple access to 1,2-aminoalcohols.
Rearrangements of Nitrile-Stabilized Ammonium Ylides
2014
Rearrangements of nitrile-stabilized ammonium ylides are useful reactions for the construction of alkylamines, nitrogen heterocycles, or carbonyl compounds. In spite of their attractive synthetic potential, they are much less frequently used than rearrangements of ammonium ylides either carrying charge-stabilizing carbonyl groups or being devoid of additional stabilization of the negative charge. This review focuses on different classes of rearrangements of nitrile-stabilized ammonium ylides as well as their application in synthetic organic chemistry. 1 Introduction 2 [1,2]-Stevens Rearrangements 3 [2,3]-Sommelet–Hauser Rearrangement 4 [2,3]-Stevens Rearrangements 5 Competitive [1,2]-, [2,3…
ChemInform Abstract: Unique Regioselectivity in the C(sp3)-H α-Alkylation of Amines: The Benzoxazole Moiety as a Removable Directing Group.
2015
The benzoxazol-2-yl substituent is easily introduced by oxidative coupling or nucleophilic substitution and can be removed by hydroxide or by hydride reduction.
Selective C-H Activation of Methoxy Groups in a Three-Component Photoreaction.
2015
Surprisingly, the photocatalytic activation of ethers by H-abstraction and addition of the generated radicals to iminium ions formed in situ from aldehydes and anilines predominantly yielded the products of methoxy activation for dimethoxymethane and 1,2-dimethoxyethane. Various anilines and aromatic as well as aliphatic aldehydes are suitable reaction partners for this three-component photoreaction (Porta-type process) which also provides a simple access to 1,2-aminoalcohols.
A one-pot cascade to protoberberine alkaloids via Stevens rearrangement of nitrile-stabilized ammonium ylides.
2015
A facile one-pot synthesis of protoberberines from readily accessible 1,2,3,4-tetrahydroisoquinoline-1-carbonitriles and 1,2-bis(bromomethyl)arenes is described. The reaction cascade comprises four consecutive transformations, all of which can be effected under a single set of conditions. Ten protoberberines, including the alkaloids pseudopalmatine and pseudoepiberberine, were prepared in yields up to 86% according to this strategy. No chromatographic purification of the products is required, and the route is devoid of any protecting group manipulations.
ChemInform Abstract: Light Induced C-C Coupling of 2-Chlorobenzazoles with Carbamates, Alcohols, and Ethers.
2016
A light induced, transition-metal-free C-C coupling reaction of 2-chlorobenzazoles with aliphatic carbamates, alcohols, and ethers is presented. Inexpensive reagents, namely sodium acetate, benzophenone, water, and acetonitrile, are employed in a simple reaction protocol using a cheap and widely available 25 W energy saving UV-A lamp at ambient temperature.
Light Induced C-C Coupling of 2-Chlorobenzazoles with Carbamates, Alcohols, and Ethers.
2016
A light induced, transition-metal-free C-C coupling reaction of 2-chlorobenzazoles with aliphatic carbamates, alcohols, and ethers is presented. Inexpensive reagents, namely sodium acetate, benzophenone, water, and acetonitrile, are employed in a simple reaction protocol using a cheap and widely available 25 W energy saving UV-A lamp at ambient temperature.
ChemInform Abstract: A One-Pot Cascade to Protoberberine Alkaloids via Stevens Rearrangement of Nitrile-Stabilized Ammonium Ylides.
2015
This method gives access to quaternary protoberberines including naturally occurring pseudopalmatine (IIIf) and pseudoepiberberine (IIIg).
ChemInform Abstract: Rearrangements of Nitrile-Stabilized Ammonium Ylides
2014
Rearrangements of nitrile-stabilized ammonium ylides are useful reactions for the construction of alkylamines, nitrogen heterocycles, or carbonyl compounds. In spite of their attractive synthetic potential, they are much less frequently used than rearrangements of ammonium ylides either carrying charge-stabilizing carbonyl groups or being devoid of additional stabilization of the negative charge. This review focuses on different classes of rearrangements of nitrile-stabilized ammonium ylides as well as their application in synthetic organic chemistry. 1 Introduction 2 [1,2]-Stevens Rearrangements 3 [2,3]-Sommelet–Hauser Rearrangement 4 [2,3]-Stevens Rearrangements 5 Competitive [1,2]-, [2,3…