标题:Transition metal-free direct dehydrogenative arylation of activated C(sp(3))-H bonds: synthetic ambit and DFT reactivity predictions
作者:Lovato, Kaitlyn; Guo, Lirong; Xu, Qing-Long; Liu, Fengting; Yousufuddin, Muhammed; Ess, Daniel H.; Kurti, Laszlo; Gao, Hongyin
作者机构:[Guo, Lirong; Liu, Fengting; Gao, Hongyin] Shandong Univ, Sch Chem & Chem Engn, Key Lab Colloid & Interface Chem, Minist Educ, Jinan 250100, Shandong, 更多
通讯作者:Gao, HY;Kurti, L;Ess, DH;Ess, Daniel H
通讯作者地址:[Gao, HY]Shandong Univ, Sch Chem & Chem Engn, Key Lab Colloid & Interface Chem, Minist Educ, Jinan 250100, Shandong, Peoples R China;[Kurti, L]Rice Un 更多
来源:CHEMICAL SCIENCE
出版年:2018
卷:9
期:41
页码:7992-7999
DOI:10.1039/c8sc02758g
摘要:A transition metal-free dehydrogenative method for the direct mono-arylation of a wide range of activated C(sp(3))-H bonds has been developed. This operationally simple and environmentally friendly aerobic arylation uses tert-BuOK as the base and nitroarenes as electrophiles to prepare up to gram quantities of structurally diverse sets (>60 examples) of alpha-arylated esters, amides, nitriles, sulfones and triaryl methanes. DFT calculations provided a predictive model, which states that substrates containing a C(sp(3))-H bond with a sufficiently low pK(a) value should readily undergo arylation. The DFT prediction was confirmed through experimental testing of nearly a dozen substrates containing activated C(sp(3))-H bonds. This arylation method was also used in a one-pot protocol to synthesize over twenty compounds containing all-carbon quaternary centers.
收录类别:EI;SCOPUS;SCIE
资源类型:期刊论文
原文链接:https://www.scopus.com/inward/record.uri?eid=2-s2.0-85055645150&doi=10.1039%2fc8sc02758g&partnerID=40&md5=c985804b3bf76b2875972e6e1a237af0
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