Multidimensional SuFEx Click Chemistry: Sequential Sulfur(VI) Fluoride Exchange Connections of Diverse Modules Launched From An SOF(4) Hub.
Multidimensional SuFEx Click Chemistry: Sequential Sulfur(VI) Fluoride Exchange Connections of Diverse Modules Launched From An SOF(4) Hub.
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DOI：
10.1002/anie.201611048
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发表时间：
2017-03-06
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影响因子：
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通讯作者：
Sharpless KB
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作者：
Li S;Wu P;Moses JE;Sharpless KB
硫（VI）氟化物交换（SuFEx）是一种新的基于点击化学的转换家族，其能够通过S（VI）枢纽合成共价连接的模块。在这里，我们报告四氟化硫（SOF 4）作为第一个多维SuFEx连接器。SOF 4位于商业上大规模生产的气体SF6和SO2 F2之间，并且像它们一样，很容易大规模合成。在SuFEx催化条件下，SOF 4可靠地寻找1º-氨基[R-NH 2]，并通过四面体亚氨基硫（VI）-连接永久锚定：R-N=（O=）S（F）2。侧，前手性二氟基团R-N=（O=）SF 2，反过来，提供了两个进一步的SuFExable处理，可以顺序交换，以创建三维共价偏离矢量从四面体硫-（VI）-枢纽。硫（VI）氟化物交换（SuFEx）是一种无金属、多连接的点击化学技术，允许通过S（VI）枢纽完美合成共价连接的模块。我们报告SOF 4（四氟化亚硫酰）作为第一个多维连接气体的SuFEx点击化学。通过可靠地寻找“1º-氨基[R-NH 2]"，SOF 4通过四面体亚氨基-硫-（VI）-键：R-N=（O=）S（F）2永久固定。二氟化物侧基R-N=（O=）SF 2又提供了两个进一步的SuFExable和前手性S-F键，它们可以依次交换以从四面体硫-（VI）-中心产生三维共价偏离矢量。
Sulfur(VI) Fluoride Exchange (SuFEx) is a new family of click-chemistry based transformations that enables the synthesis of covalently linked modules via S(VI) hubs. Here we report on 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 1º-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. Sulfur(VI) Fluoride Exchange (SuFEx) is a metal free, multi-connective click chemistry technology, allowing the flawless synthesis of covalently linked modules via S(VI) hubs. We report SOF4 (Thionyl tetrafluoride) as the first multidimensional connective gas for SuFEx click chemistry. Reliably seeking out “1º-amino groups [R-NH2]”,, SOF4 becomes permanently anchored via a tetrahedral imino-sulfur-(VI)-link: R–N=(O=)S(F)2. The pendant difluoride groups R–N=(O=)SF2, in turn, offer two further SuFExable and prochiral S-F bonds, which can be sequentially exchanged to create 3-dimensional covalent departure vectors from the tetrahedral sulfur-(VI)-hub.