Recent advances in nickel-catalyzed reductive hydroalkylation and hydroarylation of electronically unbiased alkenes
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cent advances in nickel-catalyzed reductive hydroalkylation and hydroarylation of electronically unbiased alkenes *
Xiao-Xu Wang, Xi Lu , Yan Li, Jia-Wang Wang & Yao Fu
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Hefei National Laboratory for Physical Sciences at the Microscale, CAS Key Laboratory of Urban Pollutant Conversion, Anhui Province Key Laboratory of Biomass Clean Energy, iChEM, University of Science and Technology of China, Hefei 230026, China Received June 24, 2020; accepted July 27, 2020; published online September 28, 2020
The use of simple and easily available feedstock to quickly and efficiently obtain compounds with complex molecular structures 3 3 through the transition-metal-catalyzed construction of C(sp )–C bonds has important significance. As traditional C(sp )–C coupling reagents, alkylmetallic reagents often have limitations such as air and moisture sensitivity and difficulties in storage. Nickel-catalyzed reductive olefin hydrocarbonation reactions use alkenes to replace organometallic reagents, reduce the synthesis steps, improve the functional group compatibility, and expand the substrate scope. This minireview discusses important progress in the hydroalkylation and hydroarylation of electronically unbiased alkenes in recent years and describes the key mechanism and applications. nickel, electronically unbiased alkenes, C–C bond formation, reductive hydroalkylation, reductive hydroarylation Citation:
Wang XX, Lu X, Li Y, Wang JW, Fu Y. Recent advances in nickel-catalyzed reductive hydroalkylation and hydroarylation of electronically unbiased alkenes. Sci China Chem, 2020, 63, https://doi.org/10.1007/s11426-020-9838-x
1 Introduction Transition-metal-catalyzed C–C bond formation has emerged as an important transformation strategy in organic synthetic chemistry over recent decades. Efficient construc3 tion of the C(sp ) center under mild conditions is a challenge in this area [1–3]. In recent years, nickel-catalyzed con3 struction of C(sp )–C has experienced remarkable advances because of nickel’s characteristic nature. Nickel catalysts predominantly promote the activation of alkyl electrophiles via radical catalytic cycles and effectively inhibit and/or manipulate β-H elimination reactions. Nickel catalysts also have a number of changeable valence states to flexibly participate in tandem catalytic reactions and reductive crosscoupling reactions (Scheme 1) [4–8]. Many groups, including Fu et al. [9,10], Kambe et al. [11], and Hu [12], set up leading examples and have carried out *Corresponding authors (emails: [email protected]; [email protected])
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exhaustive studies on nickel-catalyzed construction of C(sp ) centers through the coupling of alkyl or aryl electrophiles with alkylmetallic reagents. However, the required stoichiometric organometallic reagents resulted in several limitations for their wide applications. The sources of organometallic reagents are limited and need to be preprepared. Furthermore, organometallic reagents are always difficult to use and store and are sensitive to air and moisture, which results in
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