Streamlining<scp>C1</scp>Homologation Reactions Using Continuous Flow Technology: Focus on Diazomethane and Methyllithium Chemistry

Gioiello, Antimo; Ceccarelli, Giada; Colella, Marco; Luisi, Renzo

doi:10.1002/9783527830237.ch3

Homologation Reactions 2023

DOI: 10.1002/9783527830237.ch3

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StreamliningC1Homologation Reactions Using Continuous Flow Technology: Focus on Diazomethane and Methyllithium Chemistry

Antimo Gioiello

Giada Ceccarelli

Marco Colella

et al.

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Cited by 3 publications

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Carbenoids with Sulfinate as Nucleofuge for Matteson‐Type Homologation: Direct Insertion of Oxygen‐ and Nitrogen‐Substituted Units into Carbon‐Boron Bonds

Liu,

Dong

2024

Angewandte Chemie

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Carbenoid insertion into boronate carbon‐boron bonds, namely the Matteson‐type homologation, has been recognized as a powerful tool for constructing carbon‐carbon bonds. However, some limitations and inconvenience still exist with the carbenoids currently employed, such as the use of highly cryogenic and basic conditions. Herein, we report a new class of stable carbenoids with sulfinate as nucleofuge for Matteson‐type homologations, which directly introduce O‐ and N‐substituted methylenes into carbon‐boron bonds. Enabled by oxazaborolidines as the boronic substrates, the reaction is operatable at 0 °C or room temperature with weaker bases. Broad functional groups, including acidic C−H bonds, can be tolerated. The synthetic utility of this method has been demonstrated in the gram‐scale synthesis and iterative insertion of various carbenoids.

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Carbenoids with Sulfinate as Nucleofuge for Matteson‐Type Homologation: Direct Insertion of Oxygen‐ and Nitrogen‐Substituted Units into Carbon‐Boron Bonds

Liu,

Dong

2024

Angewandte Chemie

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Carbenoids with Sulfinate as Nucleofuge for Matteson‐Type Homologation: Direct Insertion of Oxygen‐ and Nitrogen‐Substituted Units into Carbon‐Boron Bonds

Liu,

Dong

2024

Angew Chem Int Ed

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Continuous Flow Generation of Highly Reactive Organometallic Intermediates: A Recent Update

Spennacchio,

Natho,

Andresini

et al. 2023

J Flow Chem

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StreamliningC1Homologation Reactions Using Continuous Flow Technology: Focus on Diazomethane and Methyllithium Chemistry

Cited by 3 publications

References 109 publications

Carbenoids with Sulfinate as Nucleofuge for Matteson‐Type Homologation: Direct Insertion of Oxygen‐ and Nitrogen‐Substituted Units into Carbon‐Boron Bonds

Carbenoids with Sulfinate as Nucleofuge for Matteson‐Type Homologation: Direct Insertion of Oxygen‐ and Nitrogen‐Substituted Units into Carbon‐Boron Bonds

Carbenoids with Sulfinate as Nucleofuge for Matteson‐Type Homologation: Direct Insertion of Oxygen‐ and Nitrogen‐Substituted Units into Carbon‐Boron Bonds

Continuous Flow Generation of Highly Reactive Organometallic Intermediates: A Recent Update

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