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471.
A visible-light-induced C-5 selective C—H borylation of imidazo[1,2-a]pyridines with NHC-BH3 via Minisci-type radical borylation reaction has been developed for the first time. The present sustainable protocol provides a new family of regioselectively C5-borylated imidazopyridines that would otherwise be difficult to prepare. It is a supplement to site-selective borylation of azines (nitrogen-containing aromatic heterocycles) and the assembly of sp2 carbon-boron bond. 相似文献
472.
Alessandro Marotta Hao Fang Callum E. Adams Kailey Sun Marcus Constantin G. Daniliuc Dr. John J. Molloy 《Angewandte Chemie (International ed. in English)》2023,62(34):e202307540
Operationally simple strategies to assemble boron containing organic frameworks are highly enabling in organic synthesis. While conventional retrosynthetic logic has engendered many platforms focusing on the direct formation of C−B bonds, α-boryl radicals have recently reemerged as versatile open-shell alternatives to access organoborons via adjacent C−C bond formation. Direct light-enabled α-activation is currently contingent on photo- or transition metal-catalysis activation to efficiently generate radical species. Here, we disclose a facile activation of α-halo boronic esters using only visible light and a simple Lewis base to enable homolytic scission. Intermolecular addition to styrenes facilitates the rapid construction of highly versatile E-allylic boronic esters. The simplicity of activation permits the strategic merger of this construct with selective energy transfer catalysis to enable the complimentary stereodivergent synthesis of Z-allylic boronic esters. 相似文献
473.
Dr. Bo Lu Dr. Lina Wang Xin Jiang Prof. Dr. Guntram Rauhut Prof. Dr. Xiaoqing Zeng 《Angewandte Chemie (International ed. in English)》2023,62(10):e202217353
The simplest diphosphene HPPH and isomeric diphosphinyldene PPH2 features prototype phosphorus-phosphorus multiple bonding properties that have been of long-standing interest in main-group chemistry. Herein, we report the observation of cis-HPPH, trans-HPPH, and PPH2 among the respective laser photolysis products of phosphine (PH3) and diphosphine (P2H4) in solid N2- and Ar-matrices at 10 K. The identification of these P2H2 isomers with matrix-isolation IR and UV/Vis spectroscopy is supported by D-isotope labeling and the quantum chemical calculations at the CCSD(T)-F12a/cc-pVTZ-F12 level using configuration-selective vibrational configuration interaction theory (VCI). Bonding analyses suggest that the two conformers of HPPH contain standard PP double bonds, whereas, PPH2 resembles P2 in having partial PP triple bond due to the H2P←P π bonding interaction. 相似文献
474.
Dr. Grant J. Sherborne Dr. Paul Kemmitt Callum Prentice Prof. Dr. Eli Zysman-Colman Prof. Dr. Andrew D. Smith Dr. Charlene Fallan 《Angewandte Chemie (Weinheim an der Bergstrasse, Germany)》2023,135(2):e202207829
Condensation of 2-vinylanilines and conjugated aldehydes followed by an efficient light-mediated cyclisation selectively yields either substituted tetrahydroquinolines with typically high dr, or in the presence of an iridium photocatalyst the synthesis of quinoline derivatives is demonstrated. These atom economical processes require mild conditions, with the substrate scope demonstrating excellent site selectivity and functional group tolerance, including azaarene-bearing substrates. A thorough experimental mechanistic investigation explores multiple pathways and the key role that imine and iminium intermediates play in the absorption of visible light to generate reactive excited states. The synthetic utility of the reactions is demonstrated on gram scale quantities in both batch and flow, alongside further manipulation of the medicinally relevant products. 相似文献
475.
Daniel Lin Matthew Coe Vinayak Krishnamurti Xanath Ispizua-Rodriguez G. K. Surya Prakash 《Chemical record (New York, N.Y.)》2023,23(9):e202300104
In the last few years, many reagents and protocols have been developed to allow for the efficient fluorofunctionalization of a diverse set of scaffolds ranging from alkanes, alkenes, alkynes, and (hetero)arenes. The concomitant rise of organofluorine chemistry and visible light-mediated synthesis have synergistically expanded the fields and have mutually benefitted from developments in both fields. In this context, visible light driven formations of radicals containing fluorine have been a major focus for the discovery of new bioactive compounds. This review details the recent advances and progress made in visible light-mediated fluoroalkylation and heteroatom centered radical generation. 相似文献
476.
Youxin Fu Jun.-Prof. Dr. Nadja A. Simeth Dr. Ryojun Toyoda Dr. Robert Brilmayer Prof. Dr. Wiktor Szymanski Prof. Dr. Ben L. Feringa 《Angewandte Chemie (International ed. in English)》2023,62(16):e202218203
Light-induced 9,10-phenanthrenequinone-electron-rich alkene ( PQ-ERA ) photocycloadditions are an attractive new type of photoclick reaction, featuring fast conversions and high biocompatibility. However, the tunability of the reaction was hardly investigated up to now. To this end, we explored the influence of substituents on both reaction partners and the reaction rate between the PQs and ERAs . We identified new handles for functionalization and discovered that using enamines as ERAs leads to drastically enhanced rates (>5400 times faster), high photoreaction quantum yields ( ΦP , up to 65 %), and multicolor emission output as well as a high fluorescence quantum yield of the adducts ( ΦF , up to 97 %). Further investigation of the photophysical and photochemical properties provided insights to design orthogonal reaction systems both in solution and on nanoparticle surfaces for ultrafast chemoselective functionalization by photoclick reactions. 相似文献
477.
Graham C. R. Ellis-Davies 《Angewandte Chemie (International ed. in English)》2023,62(9):e202206083
Light passes through biological tissue, and so it is used for imaging biological processes in situ. Such observation is part of the very essence of science, but mechanistic understanding requires intervention. For more than 50 years a “second function” for light has emerged; namely, that of photochemical control. Caged compounds are biologically inert signaling molecules that are activated by light. These optical probes enable external instruction of biological processes by stimulation of an individual element in complex signaling cascades in its native environment. Cause and effect are linked directly in spatial, temporal, and frequency domains in a quantitative manner by their use. I provide a guide to the basic properties required to make effective caged compounds for the biological sciences. 相似文献
478.
Pietro Franceschi Dr. Sara Cuadros Dr. Giulio Goti Prof. Dr. Luca Dell'Amico 《Angewandte Chemie (International ed. in English)》2023,62(8):e202217210
The synthesis of four membered heterocycles usually requires multi-step procedures and prefunctionalized reactants. A straightforward alternative is the photochemical [2+2]-heterocycloaddition between an alkene and a carbonyl derivative, conventionally based on the photoexcitation of this latter. However, this approach is limited by the absorption profile of the carbonyl, requiring in most of the cases the use of high-energy UV-light, that often results in undesired side reactions and/or the degradation of the reaction components. The development of new and milder visible light-driven [2+2]-heterocycloadditions is, therefore, highly desirable. In this Review, we highlight the most relevant achievements in the development of [2+2]-heterocycloadditions promoted by visible light, with a particular emphasis on the involved reaction mechanisms. The open challenges will also be discussed, suggesting new possible evolutions, and stimulating new methodological developments in the field. 相似文献