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Issue 68, 2014
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Lewis base mediated halogenation/semipinacol rearrangement of diazo compounds: new access to α-halo-quaternary ketones

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Abstract

A novel halogenation/semipinacol rearrangement of α-diazo alcohol catalyzed by Lewis base has been developed through a carbene-free mechanism. This semipinacol transposition, initiated by an electrophilic halogenation (X = Cl+, Br+, and I+) of diazo carbon event, furnished a convenient synthetic route for the efficient synthesis of α-halo-quaternary ketones under mild conditions.

Graphical abstract: Lewis base mediated halogenation/semipinacol rearrangement of diazo compounds: new access to α-halo-quaternary ketones

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Article information


Submitted
30 May 2014
Accepted
03 Jul 2014
First published
04 Jul 2014

Chem. Commun., 2014,50, 9773-9775
Article type
Communication
Author version available

Lewis base mediated halogenation/semipinacol rearrangement of diazo compounds: new access to α-halo-quaternary ketones

H. Mao, Z. Tang, H. Hu, Y. Cheng, W. Zheng and C. Zhu, Chem. Commun., 2014, 50, 9773
DOI: 10.1039/C4CC04154B

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