空间阻碍和缺电子的2,4,6-三叔丁基嘧啶作为π-路易斯酸对三烷基/芳基硅烷有机催化碳水化合物的硅基保护

IF 5 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2025-06-09 DOI:10.1021/acs.orglett.5c01693

Mahendra K. V. Rotta, Rupa Bai Addanki, Pavan K. Kancharla

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引用次数: 0

摘要

我们介绍了空间阻碍，张力/挫折2,4,6-三叔丁基嘧啶BArF作为醇的硅基化的温和和有效的有机催化剂。首次利用三烷基/芳基硅烷实现了碳水化合物醇的硅基保护，采用有机催化试剂，避免了通常涉及硅基卤化物和三氟酸盐的基本和恶劣条件。该方法还允许芳基酮的有机催化还原。通过各种对照实验研究了高度缺电子的2,4,6-三叔丁基嘧啶盐在保护醇类中的独特的π-酸行为。

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Sterically Hindered and Electron-Deficient 2,4,6-Tri-tert-butylpyrimidinium as a π-Lewis Acid Toward Organocatalytic Silyl Protection of Carbohydrates Using Trialkyl/aryl Silanes

We introduce the sterically hindered, strained/frustrated 2,4,6-tri-tert-butylpyrimidinium BArF as a mild and efficient organocatalyst for the silylation of alcohols. Silyl protection of carbohydrate alcohols utilizing trialkyl/aryl silanes for the first time has been achieved by employing an organocatalytic reagent, avoiding the usual basic and harsh conditions that involve silyl halides and triflates. The method also allows the organocatalytic reduction of aryl ketones. The unique π-acidic behavior of the highly electron-deficient 2,4,6-tri-tert-butylpyrimidinium salt in the protection of alcohols has been investigated via various control experiments.

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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.