This mini-review highlights the Stephenson group's contribution to the field of photoredox catalysis with emphasis on carbon-carbon bond formation. The realization of photoredox mediated reductive dehalogenation initiated investigations toward both intra- and intermolecular coupling reactions. These reactions commenced via visible light-mediated reduction of activated halogens to give carbon-centered radicals that were subsequently involved in carbon-carbon bond forming transformations. The developed protocols using Ru and Ir based polypyridyl complexes as photoredox catalysts were further tuned to efficiently catalyze overall redox neutral atom transfer radical addition reactions. Most recently, a simplistic flow reactor technique has been utilized to affect a broad scope of photocatalytic transformations with significant enhancement in reaction efficiency.
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http://dx.doi.org/10.2533/chimia.2012.394 | DOI Listing |
Anal Chem
January 2025
Beijing National Laboratory for Molecular Sciences, CAS Research/Education Center for Excellence in Molecular Sciences, Key Laboratory of Analytical Chemistry for Living Biosystems, Beijing Mass Spectrum Center, Institute of Chemistry Chinese Academy of Sciences, Beijing 100190, China.
Monounsaturated fatty acids (MUFA) are an important class of nutrients and are involved in lipid metabolism. The positions of the C=C bond and cis-trans isomerism have a significant influence on their physiological activity. However, simultaneously detecting these two structural properties has been challenging due to multiple isomers of MUFA.
View Article and Find Full Text PDFJ Am Chem Soc
January 2025
Institute of Chemical Biology, Shenzhen Bay Laboratory, Shenzhen 518132, China.
The absolute and relative configurations of bioactive chiral molecules are typically relevant to their biological properties. It is thus highly important and desirable to construct all possible stereoisomers of a lead candidate or a given bioactive natural compound. Synergistic dual catalysis has been recognized as a reliable synthetic strategy for a variety of predictable stereodivergent transformations.
View Article and Find Full Text PDFJ Am Chem Soc
January 2025
Department of Chemistry, Queen's University, Kingston, ON K7L 3N6, Canada.
Tambjamines are complex bipyrrole-containing natural products that possess promising bioactive properties. Although is known to produce both cyclic tambjamine MYP1 and the linear precursor (YP1), the biosynthetic machinery used to catalyze the site-selective oxidative carbocyclization at the unactivated 1° carbon of YP1 has remained unclear. Here, we demonstrate that a three-component Rieske system consisting of an oxygenase (TamC) and two redox partner proteins is responsible for this unprecedented activity on YP1 and potentially, a non-native substrate (BE-18591).
View Article and Find Full Text PDFMolecules
January 2025
Department of Chemistry, Fudan University, Shanghai 200438, China.
This review highlights significant advances in iron-catalyzed cross-dehydrogenative coupling (CDC), a method pivotal for forming carbon-carbon (C-C) bonds directly from C-H bonds. This technique uses iron-a naturally abundant, inexpensive, and environmentally benign transition metal-as a catalyst to facilitate the coupling of two unfunctionalized C-H bonds. This method stands out for avoiding pre-functionalized substrates, reducing both waste and cost in organic synthesis.
View Article and Find Full Text PDFNat Commun
January 2025
School of Materials Science and Chemical Engineering, Institute of Drug Discovery Technology, Institute of Mass Spectrometry, Zhejiang Engineering Research Center of Advanced Mass Spectrometry and Clinical Application, Ningbo University, Ningbo, PR China.
C-C bond cleavage and recombination provide an efficient strategy for the modification and reconstruction of molecule structures. Herein, we present a method for achieving amidation of aryl C(sp)-H bond through the cleavage and recombination of C-C triple bond with the involvement of nitrous acid esters. This method marks the instance of precise and controlled stepwise cleavage of C-C triple bond, offering a fresh perspective for the cleavage of such bonds.
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