Anion Mask Strategy Enabling Organolithium Species Bearing Formyl Groups: Protecting-Group-Free Synthesis for Unsymmetric Dicarbonyl Arenes

Yosuke Ashikari

doi:10.1021/acs.joc.6c00108

Anion Mask Strategy Enabling Organolithium Species Bearing Formyl Groups: Protecting-Group-Free Synthesis for Unsymmetric Dicarbonyl Arenes

2026-04-01

0

PRE

AI

Y

Yosuke Ashikari

K

Kikuchi, Ryuhei

A

Adachi, Moe

H

Hiroki Soutome

A

Aiichiro Nagaki *

DOI：10.1021/acs.joc.6c00108

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Abstract

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The protecting groups for carbonyl groups, in particular, a formyl group, are one of the milestones of recent organic synthesis but today are treated as a limitation in terms of step economy. Herein, we report a novel strategy for treating carbonyl groups as nucleophile-tolerant functional groups. Utilizing amino groups as poor leaving groups, masked carbonyl groups were designed and were monitored by in-line analyses. We achieved lithiation of aryl bromide bearing masked carbonyl groups, followed by reactions with electrophiles. With this strategy, we demonstrated syntheses of unsymmetric dicarbonyl arenes, which basically require protecting groups.

Keywords:

MAGNESIUM REAGENTS

ARYL-MAGNESIUM

FLOW

CHEMISTRY

LICL

Anion Mask Strategy Enabling Organolithium Species Bearing Formyl Groups: Protecting-Group-Free Synthesis for Unsymmetric Dicarbonyl Arenes

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Organization

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