Two Green Protocols for Halogenative Semipinacol Rearrangement

Two Green Protocols for Halogenative Semipinacol Rearrangement

Semipinacol rearrangement is a special type of Wagner–Meerwein rearrangement that involves carbocation 1,2-rearrangement to provide carbonyl compounds with an α-quaternary carbon center. It has been strategically used for natural product synthesis and construction of highly congested quaternary carb...

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Veröffentlicht in:Journal of organic chemistry 2023-01, Vol.88 (1), p.504-512
Hauptverfasser: Song, Liyan, Zhou, Yiqin, Liang, Hanbin, Li, Hongzuo, Lai, Yunrong, Yao, Hongliang, Lin, Ran, Tong, Rongbiao
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Sprache:eng
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Cyclization
Cyclohexenes
Hydrogen Peroxide
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container_end_page 512
container_issue 1
container_start_page 504
container_title Journal of organic chemistry
container_volume 88
creator Song, Liyan
Zhou, Yiqin
Liang, Hanbin
Li, Hongzuo
Lai, Yunrong
Yao, Hongliang
Lin, Ran
Tong, Rongbiao
description Semipinacol rearrangement is a special type of Wagner–Meerwein rearrangement that involves carbocation 1,2-rearrangement to provide carbonyl compounds with an α-quaternary carbon center. It has been strategically used for natural product synthesis and construction of highly congested quaternary carbons. Herein, we report a safe and green protocol that uses oxone/halide and Fenton bromide to achieve halogenative semipinacol rearrangement. The key feature of this method is the green in situ generation of reactive halogenating species from oxidation of halide with oxone or H2O2, which produces a nontoxic byproduct (potassium sulfate or water). Easy operation (insensitive to air and moisture) at room temperature without using special equipment adds additional advantage over previous methods.
doi_str_mv 10.1021/acs.joc.2c02496
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subjects Cyclization
Cyclohexenes
Hydrogen Peroxide
title Two Green Protocols for Halogenative Semipinacol Rearrangement
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