Harbin Institute of Technology
ORCID: 0000-0001-9396-9520Publishes on Radical Photochemical Reactions, Catalytic C–H Functionalization Methods, Crystallization and Solubility Studies. 314 papers and 7.1k citations.
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The functionalization of C-H bonds and the visible light photoredox catalysis represent two prominent challenges in organic chemistry. In this regard, the combination of visible-light catalysis and C-H bond functionalization adjacent to a tertiary amine has been successfully developed in the past three years. In this tutorial review, we aim to give a brief overview of this issue and state the main results obtained in the reactions.
This review highlights the recent advances in cross-dehydrogenative amination for C–N bond construction from C–H/N–H cross-coupling partners through photocatalytic and/or electronic techniques.
Catalytic C(sp3)–H functionalization has provided enormous opportunities to construct organic molecules, facilitating the derivatization of complex pharmaceutical compounds. Within this framework, direct hydrogen atom transfer (HAT) photocatalysis becomes an appealing approach to this goal. However, the viable substrates utilized in these protocols are limited, and the site selectivity shows preference to activated and thermodynamically favored C(sp3)–H bonds. Herein, we describe the development of undirected iron-catalyzed C(sp3)–H borylation, thiolation, and sulfinylation reactions enabled by the photoinduced ligand-to-metal charge transfer (LMCT) process. These reactions exhibit remarkably broad substrate scope (>150 examples in total), and most importantly, all of these three reactions show unconventional regioselectivity, with the occurrence of C(sp3)–H borylation, thiolation, and sulfinylation preferentially at the distal methyl position. The procedures are operationally simple and readily scalable and provide access to high-value products from simple hydrocarbons in one step. Mechanistic studies and control experiments indicate that the afforded site selectivity is not only relevant to the HAT species but also largely affected by the use of boron- and sulfone-based radical acceptors.
A new method for intermolecular sp3-sp3 C-C bond formation between primary aliphatic alcohol and olefin by use of a RhCl(PPh3)3 (cat.)/BF3.OEt2 (2.5 equiv)/BuBr (0.5 equiv)/toluene system was first disclosed, which possessed quite significant utilities for organic synthesis, especially for that of secondary alcohols. The most significant aspect is the discovery that rhodium-catalyzed C-H bond activation of alcohols is feasible under Lewis acid-promoted conditions.