Temporary Intramolecular Generation of Pyridine Carbenes in Metal‐Free Three‐Component CH Bond Functionalisation/Aryl‐Transfer Reactions

The photolysis of donor–acceptor diazoalkanes in the presence of propargylic alcohols furnishes valuable, sterically demanding tetra-substituted cyclopropenes in high yield under metal-free conditions.

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Metal-Free Addition of Boronic Acids to Silylnitronates

Synlett ◽

10.1055/s-0039-1690845 ◽

2020 ◽

Vol 31 (09) ◽

pp. 856-860

Author(s):

Laurent El Kaïm ◽

Mansour Dolé Kerim ◽

Pakoupati Boyode ◽

Julian Garrec

Keyword(s):

Reaction Mechanism ◽

Double Bond ◽

Boronic Acids ◽

Dft Study ◽

Metal Free ◽

Nitro Derivatives ◽

Oxime Derivatives ◽

Nitrogen Double Bond ◽

First Time ◽

Aryl Transfer

We report for the first time a metal-free addition of boronic acids to silylnitronates to afford oxime derivatives through aryl transfer on the carbon nitrogen double bond. A reaction mechanism has been proposed in relation with a DFT study on the key aryl transfer. This arylation process is effective for cycloalkenyl nitro derivatives leading to oximes that may be oxidatively converted into 3-arylisoxazole derivatives.

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Enantioselective synthesis of gem-diarylalkanes by transition metal-catalyzed asymmetric arylations (TMCAAr)

Chemical Science ◽

10.1039/c7sc03404k ◽

2018 ◽

Vol 9 (3) ◽

pp. 546-559 ◽

Cited By ~ 30

Author(s):

Tao Jia ◽

Peng Cao ◽

Jian Liao

Keyword(s):

Transition Metal ◽

Enantioselective Synthesis ◽

Transfer Reactions ◽

Stereogenic Centers ◽

Transition Metal Catalyzed ◽

Metal Catalyzed ◽

Quaternary Stereogenic Centers ◽

Aryl Transfer

To date, enantiomerically enriched molecules containing gem(1,1)-diaryl containing tertiary or quaternary stereogenic centers have been readily accessed by transition metal-catalyzed enantioselective or stereoconvergent aryl transfer reactions.

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ChemInform Abstract: Tropos Amino Alcohol Mediated Enantioselective Aryl Transfer Reactions to Aromatic Aldehydes.

ChemInform ◽

10.1002/chin.201512037 ◽

2015 ◽

Vol 46 (12) ◽

pp. no-no

Author(s):

Laura Pisani ◽

Carmela Bochicchio ◽

Stefano Superchi ◽

Patrizia Scafato

Keyword(s):

Amino Alcohol ◽

Aromatic Aldehydes ◽

Transfer Reactions ◽

Aryl Transfer

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Modifications of amino acids using arenediazonium salts

Organic & Biomolecular Chemistry ◽

10.1039/c9ob01471c ◽

2019 ◽

Vol 17 (36) ◽

pp. 8308-8329 ◽

Cited By ~ 3

Author(s):

Saumitra Sengupta ◽

Srinivasan Chandrasekaran

Keyword(s):

Amino Acids ◽

Chemical Biology ◽

Transfer Reactions ◽

Arenediazonium Salts ◽

Aryl Transfer

Aryl transfer reactions from arenediazonium salts have started to make their impact in chemical biology with initial forays in the arena of arylative modifications and bio-conjugations of amino acids, peptides and proteins.

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