Cytochromes P450 (P450s or CYPs) are versatile biocatalysts capable of realizing a broad range of synthetically challenging reactions. The development of synthetic catalysts/catalytic systems that model the enzyme function is a goal that has long been pursued. In this account, we mainly summarize our latest advances in the field of P450s-inspired catalysis, including reductive activation strategy for highly efficient oxidations and an unusual L-cystine-derived ligand as the model of the P450s for highly efficient iron-catalyzed undirected arene C-H hydroxylation. These new paradigms exhibit some catalytic properties of P450s, such as effective late-stage functionalization of complex targets, good reactive functional group tolerance, and high catalytic efficiency and selectivity. 1. Introduction 2. Reductive activation strategy for oxygenation 3. Fe/Cysteine-based ligand as a biomimetic model of P450 for arene C-H hydroxylation 4. Conclusion
A highly efficient, practical, and ligand-free palladium-catalyzed carbonylation of aryl iodides with alkenylboronic acids has been developed. A variety of chalcones and ɑ-branched enones were isolated in satisfactory to good yields with good substrates compatibilities under ambient pressure of CO and room temperature. Moreover, a substoichiometric amount of base renders the transformation to proceed well. The merit of this strategy as a late-stage functionalization platform has been demonstrated by the modification of an estrone- and a 3-phenyl-L-alanine -derived complex substrates.
Among diverse CH bonds, direct functionalization of the benzylic position is particularly fascinating but a challenging process for synthetic chemists because alkyl arenes are abundant, cheap, and stable and at the same time suffer from issues of selectivity, functional group compatibility, and inclination toward over oxidation in benzylic CH functionalization. Among various transition metals, iron ideally conforms to the spirit of element strategy initiative. Hence, iron‐catalyzed benzylic CH functionalization has emerged as an area of significant interest to researchers. We will endeavor to highlight the recent advances in iron‐catalyzed benzylic CH functionalization for constructing CC, CN, and CO bonds. We hope that this review will be useful for synthetic organic chemists and inspire further discoveries in the interesting iron‐catalyzed CH functionalization area.
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