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Convergent Synthesis of Fluoroalkenes Using a Dual-Reactive Unit
The Journal of Organic Chemistry ( IF 3.6 ) Pub Date : 2021-01-05 , DOI: 10.1021/acs.joc.0c02474 Motoyuki Isoda 1, 2 , Yuta Uetake 2 , Tadashi Takimoto 1 , Junpei Tsuda 1, 2 , Takamitsu Hosoya 1, 2, 3 , Takashi Niwa 1, 2
The Journal of Organic Chemistry ( IF 3.6 ) Pub Date : 2021-01-05 , DOI: 10.1021/acs.joc.0c02474 Motoyuki Isoda 1, 2 , Yuta Uetake 2 , Tadashi Takimoto 1 , Junpei Tsuda 1, 2 , Takamitsu Hosoya 1, 2, 3 , Takashi Niwa 1, 2
Affiliation
Fluoroalkenes have shown importance as a metabolically stable isostere of amide compounds. To expedite the synthesis of diverse fluoroalkenes, we have developed a dual-reactive C2-unit, (Z)-1-boryl-1-fluoro-2-tosyloxyethene, containing nucleophilic and electrophilic moieties. Consecutive palladium-catalyzed cross-coupling reactions of this unit with aryl bromides and aryl boronic acids allow for the convergent synthesis of diverse trans-1,2-diaryl-substituted fluoroethenes in a chemoselective and stereoretentive manner.
中文翻译:
双反应单元聚合合成氟代烯烃
氟代烯烃已显示出作为酰胺化合物代谢稳定的等排体的重要性。为了加快各种氟代烯烃的合成,我们开发了一种双反应性C2-单元(Z)-1-硼基-1-氟-2-甲苯磺酰氧基乙烯,其中含有亲核和亲电部分。该单元与芳基溴化物和芳基硼酸的连续钯催化的交叉偶联反应允许以化学选择性和立体保持方式聚合合成各种反式-1,2-二芳基取代的氟乙烯。
更新日期:2021-01-16
中文翻译:
双反应单元聚合合成氟代烯烃
氟代烯烃已显示出作为酰胺化合物代谢稳定的等排体的重要性。为了加快各种氟代烯烃的合成,我们开发了一种双反应性C2-单元(Z)-1-硼基-1-氟-2-甲苯磺酰氧基乙烯,其中含有亲核和亲电部分。该单元与芳基溴化物和芳基硼酸的连续钯催化的交叉偶联反应允许以化学选择性和立体保持方式聚合合成各种反式-1,2-二芳基取代的氟乙烯。