Electrocatalytic C–H Activation,ACS Catalysis

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Electrocatalytic C–H Activation
ACS Catalysis ( IF 11.3 ) Pub Date : 2018-06-18 00:00:00 , DOI: 10.1021/acscatal.8b01682
Nicolas Sauermann ₁ , Tjark H. Meyer ₁ , Youai Qiu ₁ , Lutz Ackermann ₁

Affiliation

C–H activation has emerged as a transformative tool in molecular synthesis, but until recently oxidative C–H activations have largely involved the use of stoichiometric amounts of expensive and toxic metal oxidants, compromising the overall sustainable nature of C–H activation chemistry. In sharp contrast, electrochemical C–H activation has been identified as a more efficient strategy that exploits storable electricity in place of byproduct-generating chemical reagents. Thus, transition-metal catalysts were shown to enable versatile C–H activation reactions in a sustainable manner. While palladium catalysis set the stage for C(sp²)–H and C(sp³)–H functionalizations by N-containing directing groups, rhodium and ruthenium catalysts allowed the use of weakly coordinating amides and acids. In contrast to these precious 4d transition metals, the recent year has witnessed the emergence of versatile cobalt catalysts for C–H oxygenations, C–H nitrogenations, and C–C-forming [4+2] alkyne annulations. Thereby, the use of toxic and expensive silver(I) oxidants was prevented, improving the environmentally benign nature of C–H activation catalysis. Herein, we summarize the recent major advances in organometallic activations of otherwise inert C–H bonds by electrocatalysis through May 2018.

中文翻译：

电催化CH活化

C–H活化已成为分子合成中的一种转化工具，但是直到最近，氧化的C–H活化很大程度上涉及化学计量的昂贵和有毒金属氧化剂的使用，从而损害了C–H活化化学的整体可持续性。与之形成鲜明对比的是，电化学C–H活化被认为是一种更有效的策略，它利用可储存的电代替产生副产物的化学试剂。因此，显示出过渡金属催化剂能够以可持续的方式实现多种CH活化反应。钯催化为C（sp ²）–H和C（sp ³）–通过含氮的导向基团，铑和钌催化剂的H官能化，可以使用弱配位的酰胺和酸。与这些珍贵的4d过渡金属相反，近年来见证了用于C–H氧合，C–H硝化和C–C形成[4 + 2]炔烃环合的多功能钴催化剂的出现。因此，可以避免使用有毒且昂贵的银（I）氧化剂，从而改善了C–H活化催化的环境友好性。在此，我们总结了直到2018年5月通过电催化对否则呈惰性的C–H键进行有机金属活化的最新进展。

更新日期：2018-06-18

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