Full Professor, Wuhan University
Address: The Institute for Advanced Studies (高等研究院),
Wuhan University, Wuhan 430072, P. R. China
Office: 205, Jijian Building
Lab: 515, Dangdai Building
Email: gci2011@whu.edu.cn
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X. Zheng#, P. Peng#, C. Huang, Q. Lu* ___________________________________________________________________________
Sustainable and site-selective C-H functionalization is still a challenge because of the comparable properties of bonds of the same type. Here, an electrochemical C(sp2)-H/C(sp3)-H coupling with aryl iodides is reported for the first time. The C(sp2)-H bond outperformed the much weaker C(sp2)-I bond in participation in C(sp2)-H/C(sp3)-H coupling. This protocol features mild reaction conditions, good functional-group tolerance and scalability. Cross-coupling products with C-I bonds are versatile moieties for further synthetic manipulation, they can undergo Suzuki, Sonogashira, Ullmann-Ma, Catellani, and Heck reactions etc to introduce new functional groups into target molecules with good yields. Mechanistic investigations showed that the site selectivity of the reaction is enabled by an iodine-assisted [3,3]-sigmatropic rearrangement, and the interaction of hypervalent iodine generated in situ with an enolate is the rate-determining step.
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C. Huang, W. Ma, X. Zheng, M. Xu, X. Qi, * Q. Lu* ___________________________________________________________________________
Selective hydrogenation of
epoxides would be a direct and powerful approach for alcohol synthesis, but it
has proven to be elusive. Here, electrochemically epoxide hydrogenation using
electrons and protons as reductants is reported. A wide range of primary,
secondary, and tertiary alcohols can be achieved through selective Markovnikov
or anti-Markovnikov ring opening in the absence of transition metals.
Mechanistic investigations revealed that the regioselectivity is controlled by
the thermodynamic stabilities of the in situ generated benzyl radicals for
aryl-substituted epoxides and the kinetic tendency for Markovnikov selective
ring opening for alkyl-substituted epoxides.
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B. Wang#, P. Peng#, W. Ma, Z. Liu, C. Huang, Y. Cao, P. Hu, X. Qi, * Q. Lu* __________ _________________________________________________________________
Herein, a fast, scalable, and transition-metal-free borylation of alkyl halides (X = I, Br, Cl) enabled by electroreduction is reported. This process provides an efficient and practical access to primary, secondary, and tertiary boronic esters at a high current. More than 70 examples, including the late-stage borylation of natural products and drug derivatives, are furnished at room temperature, thereby demonstrating the broad utility and functional-group tolerance of this protocol. Mechanistic studies disclosed that B2cat2 serves as both a reagent and a cathodic mediator, enabling electroreduction of difficult-to-reduce alkyl bromides or chlorides at a low potential.
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