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Transition Metal-Catalyzed Cross-Couplings of Benzylic Sulfone Derivatives
The Chemical Record ( IF 6.6 ) Pub Date : 2021-09-15 , DOI: 10.1002/tcr.202100210
Masakazu Nambo 1 , Cathleen M Crudden 1, 2
Affiliation  

In recent years, the use of organosulfones as a new class of cross-coupling partner in transition-metal catalyzed reactions has undergone significant advancement. In this personal account, our recent investigations into desulfonylative cross-coupling reactions of benzylic sulfone derivatives catalyzed by Pd, Ni, and Cu catalysis is described. Combined with the facile α-functionalizations of sulfones, our methods can be used to form valuable multiply-arylated structures such as di-, tri-, and, tetraarylmethanes from readily available substrates. The reactivity of sulfones can be increased by introducing electron-withdrawing substituents such as 3,5-bis(trifluoromethyl)phenyl and trifluoromethyl groups, which enable more challenging cross-coupling reactions. Reactive intermediates including Cu-carbene complexes were identified as key intermediates in sulfone activation, representing new types of C−SO2 bond activation processes. These results indicate sulfones are powerful functional groups, enabling new catalytic desulfonylative transformations.

中文翻译:

过渡金属催化的苄基砜衍生物的交叉偶联

近年来,在过渡金属催化反应中使用有机砜作为一类新的交叉偶联伙伴取得了重大进展。在这个个人帐户中,我们描述了我们最近对 Pd、Ni 和 Cu 催化的苄基砜衍生物的脱磺酰交叉偶联反应的研究。结合砜的简单 α-官能化,我们的方法可用于从容易获得的底物形成有价值的多芳基化结构,例如二、三和四芳基甲烷。可以通过引入吸电子取代基(例如 3,5-双(三氟甲基)苯基和三氟甲基)来提高砜的反应性,从而实现更具挑战性的交叉偶联反应。2键活化过程。这些结果表明砜是强大的官能团,能够实现新的催化脱磺酰化转化。
更新日期:2021-09-15
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