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The C(sp3)–H bond is found widely in organic molecules. Recently, the functionalization of C(sp3)–H bonds has developed into a powerful tool for augmenting highly functionalized frameworks in organic synthesis. Based on the results obtained in our group, the present account mainly summarizes recent progress on the functionalization of C(sp3)–H bonds of aliphatic alcohols, ketones, alkyl nitriles, and ethers with styrene or cinnamic acid using tert-butyl hydroperoxide (TBHP) as a radical initiator.1 Introduction2 Oxidative Coupling of Styrenes with C(sp3)–H Bonds3 Decarboxylative Cross-Couplings of α,β-Unsaturated Carboxylic Acids with C(sp3)–H Bonds4 Conclusions

NAD(P)H and NAD+ have a significant role in biochemistry, and many NAD(P)H models received particular attention. Research in NADH models mainly focuses on asymmetric reduction and life sciences. Over the past few decades, a particularly large number of new chiral NAD(P)H models have appeared, and there have been significant developments in this area. We summarized advanced research in chiral NAD(P)H models in this paper. These models not only show very good performance in asymmetric reduction, but also have excellent fluorescence features. In addition, we present a discussion about some recent studies on the asymmetric reduction of NAD(P)H-dependent dehydrogenase, and we open a new door on research into NAD(P)H models. At last, some advances focused on the fluorescence phenomenon of some chiral NAD(P)H models have also been summarized. 1 Introduction 2 NAD(P)H Models with Symmetric Structure 2.1 Chiral NAD(P)H Models with C 1 Symmetry 2.2 Chiral NAD(P)H Models with C 2 Symmetry 2.3 Chiral NAD(P)H Models with C 3 Symmetry 3 Symmetric Reduction 3.1 Effect of the Substituents of Dihydronicotinamide 3.2 Effect of the C-4 Substituent of Dihydropyridine 3.3 Special Structures 3.4 Applying Dehydrogenase to Biocatalytic Asymmetric Reductions with NADPH 4 Fluorescence Properties 5 Conclusion

Transition-metal-catalyzed direct carbon–hydrogen bond functionalization has made significant advances in the field of carbon–hydrogen bond activation over the past decades. This methodology has the potential to be used in many different areas of chemistry; for example, it can provide an opportunity for the synthesis of various kinds of complex compounds. This account mainly focuses on recent advances in transition-metal-catalyzed direct sp3-carbon–hydrogen bond functionalization to form carbon–carbon bonds. 1 Introduction 2 Carbon–Carbon Bond Formation via Direct sp3-Carbon–Hydrogen Bond Functionalization 2.1 Coupling of sp3-Carbon–Hydrogen and sp-Carbon–Hydrogen Bonds 2.2 Coupling of sp3-Carbon–Hydrogen and sp2-Carbon–Hydrogen Bonds 2.3 Coupling of sp3-Carbon–Hydrogen and sp3-Carbon–Hydrogen Bonds 2.4 Coupling of sp3-Carbon–Hydrogen and C–X Bonds 3 Conclusion