Access to Diarylmethanols by Wittig Rearrangement of ortho-, meta-, and para-Benzyloxy-N-Butylbenzamides.

Access to Diarylmethanols by Wittig Rearrangement of ortho-, meta-, and para-Benzyloxy-N-Butylbenzamides.
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DOI:
10.1021/acs.joc.1c03160
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发表时间:
2022-04-01
影响因子:
3.6
通讯作者:
Slawin, Alexandra M. Z.
Slawin, Alexandra M. Z.
中科院分区:
化学2区
文献类型:
--
作者:
Aitken, R. Alan;Harper, Andrew D.;Inwood, Ryan A.;Slawin, Alexandra M. Z.

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已发现N-丁基酰胺基团CONHBu是芳基苄基醚的[1,2]-Wittig重排的有效促进剂,从而允许从简单的羟基苯甲酸衍生物开始的异构纯的取代的二芳基甲醇的两步合成。该方法与包括甲基、甲氧基和氟在内的宽范围的官能团相容,但不与硝基相容,并且出乎意料地,该方法适用于Meta以及邻位和帕拉异构体系列。
The N-butyl amide group, CONHBu, has been found to be an effective promoter of the [1,2]-Wittig rearrangement of aryl benzyl ethers and thus allow the two-step synthesis of isomerically pure substituted diarylmethanols starting from simple hydroxybenzoic acid derivatives. The method is compatible with a wide range of functional groups including methyl, methoxy, and fluoro, although not with nitro and, unexpectedly, is applicable to meta as well as ortho and para isomeric series.
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