Multidimensional SuFEx Click Chemistry: Sequential Sulfur(VI) Fluoride Exchange Connections of Diverse Modules Launched From An SOF4 Hub,Angewandte Chemie International Edition

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Multidimensional SuFEx Click Chemistry: Sequential Sulfur(VI) Fluoride Exchange Connections of Diverse Modules Launched From An SOF4 Hub
Angewandte Chemie International Edition ( IF 16.1 ) Pub Date : 2017-02-06 , DOI: 10.1002/anie.201611048
Suhua Li ₁ , Peng Wu ₂ , John E. Moses _{1,

3} , K. Barry Sharpless ₁

Affiliation

Sulfur(VI) fluoride exchange (SuFEx) is a new family of click chemistry based transformations that enable the synthesis of covalently linked modules via S^VI hubs. Here we report thionyl tetrafluoride (SOF₄) as the first multidimensional SuFEx connector. SOF₄ sits between the commercially mass‐produced gases SF₆ and SO₂F₂, and like them, is readily synthesized on scale. Under SuFEx catalysis conditions, SOF₄ reliably seeks out primary amino groups [R‐NH₂] and becomes permanently anchored via a tetrahedral iminosulfur(VI) link: R−N=(O=)S(F)₂. The pendant, prochiral difluoride groups R−N=(O=)SF₂, in turn, offer two further SuFExable handles, which can be sequentially exchanged to create 3‐dimensional covalent departure vectors from the tetrahedral sulfur(VI) hub.

中文翻译：

多维SuFEx Click化学：从SOF4集线器启动的各种模块的顺序硫（VI）氟化物交换连接

氟化硫（VI）交换（SuFEx）是基于点击化学的新型转换，可通过S ^VI集线器合成共价连接的模块。在这里，我们报告亚硫酰四氟化物（SOF ₄）作为第一个多维SuFEx连接器。SOF ₄位于商业化大量生产的气体SF ₆和SO ₂ F _2之间，并且像它们一样，很容易按比例合成。在SuFEx催化条件下，SOF ₄可靠地找出伯氨基[R- NH ₂ ]，并通过四面亚氨基亚硫（VI）链接永久锚定：RN =（O =）S（F）₂。侧链前手性二氟化物基团RN =（O =）SF ₂又提供了另外两个SuFExable句柄，可以依次交换这些句柄以从四面体硫（VI）集线器创建3维共价偏离向量。

更新日期：2017-02-06

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