Stereoselective Synthesis of (E)-α-Bromo- and (E)-α-Iodoacrylates from Readily Available tert-Butyl Diphenylphosphonoacetate

IF 5 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2025-07-24 DOI:10.1021/acs.orglett.5c02194

Kaori Ando*, Saki Ota, Miki Idota, Yutaka Semii and Natsuhisa Oka,

引用次数: 0

Abstract

tert-Butyl (diphenylphosphono)bromoacetate 3d was readily prepared by brominating tert-butyl diphenylphosphonoacetate 5d. The HWE reaction of 3d with various aldehydes gave (E)-α-bromoacrylates 1 with selectivity ranging from 89:11 to 99:1, typically in yields exceeding 90%. Additionally, the HWE reactions after treatment of 3d with NaI or iodinating 5d produced the corresponding (E)-α-iodoacrylates 7 in yields of 87–100%, with selectivities ranging from 91:9 to 99:1. The products were used to synthesize trisubstituted alkenes through Sonogashira coupling.

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二苯基膦乙酸叔丁酯立体选择性合成(E)-α-溴和(E)-α-碘丙烯酸酯。

以二苯基膦乙酸叔丁酯5d为原料，制备了二苯基膦乙酸叔丁酯3d。3d与各种醛的HWE反应得到(E)-α-溴丙烯酸酯1，选择性范围为89:11 ~ 99:1，收率一般超过90%。此外，用NaI处理3d或碘化5d后的HWE反应产生相应的(E)-α-碘丙烯酸酯7，收率为87-100%，选择性为91:9 ~ 99:1。产物经Sonogashira偶联合成三取代烯烃。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

Organic Letters 化学-有机化学

CiteScore

9.30

自引率

11.50%

发文量

1607

审稿时长

1.5 months

期刊介绍： Organic Letters invites original reports of fundamental research in all branches of the theory and practice of organic, physical organic, organometallic,medicinal, and bioorganic chemistry. Organic Letters provides rapid disclosure of the key elements of significant studies that are of interest to a large portion of the organic community. In selecting manuscripts for publication, the Editors place emphasis on the originality, quality and wide interest of the work. Authors should provide enough background information to place the new disclosure in context and to justify the rapid publication format. Back-to-back Letters will be considered. Full details should be reserved for an Article, which should appear in due course.