HCO3−-mediated highly efficient photoelectrochemical dioxygenation of arylalkenes: triple roles of HCO3−-derived radicals
文献信息
Alkene dioxygenation reactions are significant organic transformation process, but the direct oxidation of alkenes on photoanodes exhibits quite poor yields for dioxygenation products. Here, we report that the presence of bicarbonate in a heterogenous photoelectrochemical (PEC) cell can achieve efficient dioxygenation of alkenes under mild conditions. A broad range of alkene substrates with a variety of substitute groups can be effectively oxygenated to diols or α-hydroxy ketones, with a product yield of up to 89%. Furthermore, we identified that the diol product is formed via a peroxydiol intermediate. Spin-trap electron paramagnetic resonance (EPR) experiments show that the HCO3−-derived radicals are important active species. Accordingly, we propose a triple role for formed HCO3−-derived radicals in the dioxygenation of alkenes: attacking the CC bond of the alkene to initiate the reaction, producing ˙CO4− active species for the formation of a peroxydiol intermediate, and reducing the peroxydiol to a diol. The present work provides a promising strategy for the transformation of alkenes with green radicals and paves the way for the application of HCO3− in PEC organic synthesis.
相关文献
Selective aerobic oxidation in supercritical carbon dioxide catalyzed by the H5PV2Mo10O40 polyoxometalate
Galia Maayan, Benjamin Ganchegui, Ronny Neumann
DOI: 10.1039/B603148J
Hosomi–Sakurai reactions of silacyclic allyl silanes
Jonathan D. Sellars, Patrick G. Steel, Michael J. Turner
DOI: 10.1039/B602642G
Effect of residual monomer on the spectroscopic properties of polythiophenes
Yu Wang, Ashley A. Mills, William B. Euler, Brett L. Lucht
DOI: 10.1039/B600793G
Lithium ion conduction in an organoborate zwitterion–LiTFSI mixture
Asako Narita, Wataru Shibayama, Kenji Sakamoto, Tomonobu Mizumo, Noriyoshi Matsumi, Hiroyuki Ohno
DOI: 10.1039/B517019B
Insulated conducting polymers: manipulating charge transport using supramolecular complexes
Phoebe H. Kwan, Timothy M. Swager
DOI: 10.1039/B508399K
Convenient, scalable and flexible method for the preparation of imidazolium salts with previously inaccessible substitution patterns
Alois Fürstner, Manuel Alcarazo, Vincent César, Christian W. Lehmann
DOI: 10.1039/B604236H
Synthesis of organic–inorganic hybrid mesoporous tin oxophosphate in the presence of anionic surfactant
Masahiro Fujiwara, Masahiko Matsukata
DOI: 10.1039/B508589F
Characterization of the H2 sensing mechanism of Pd-promoted SnO2 by XAS in operando conditions
Thomas Neisius, Bernard Chenevier, Aleksandre M. Gaskov, Michel Labeau
DOI: 10.1039/B509826B
Towards large amounts of Janusnanoparticles through a protection–deprotection route
Stéphane Reculusa, Franck Pereira, Marie-Hélène Delville, Christophe Mingotaud, Etienne Duguet, Elodie Bourgeat-Lami, Serge Ravaine
DOI: 10.1039/B507486J
您可能还喜欢
硅烷偶联剂ZQ-172(CAS号:1067-53-4)的主要用途是什么?
硅烷偶联剂ZQ-172主要用于增强无机填料与有机高分子材料之间的相容性,常见于橡胶、塑料、涂料和胶黏剂等复合体系中。其硅氧烷基团可与玻璃纤维、二氧化硅等无机物表...
如何处理含有6-(2,4-二甲氧基苯基)-2-吡啶甲醇(CAS号:887981-31-9)的废料?
对于含有该化合物的废料,首先应收集并分类存放,避免与其它化学品混合。在处理前,需进行必要的检测,确定其含量和性质。随后,可以采用化学氧化、生物降解或物理吸附等方...
甲砜霉素甘氨酸酯盐酸盐(CAS号:2611-61-2)的物理化学性质是什么?
该化合物为白色或类白色结晶性粉末,不溶于水,溶于乙醇和氯仿。分子量为403.03 g/mol。它具有手性,含有三个手性中心,分别为2S,3R构型。该化合物在酸性...
如何储存反式-环丙烷-1,2-二胺双盐酸盐(CAS号:3187-76-6)?
反式-环丙烷-1,2-二胺双盐酸盐应存放在阴凉、干燥且通风良好的地方,避免阳光直射。储存容器应密封,以防挥发和受潮。同时,应远离火源和热源,确保储存环境温度不超...
什么是吩嗪硫酸甲酯(CAS号:299-11-6)?
吩嗪硫酸甲酯是一种有机化合物,化学结构由吩嗪环与甲酯基团构成,分子式为C10H9N2SO4。其为吩嗪类衍生物,具有典型的芳香环结构和酯基官能团,常作为氧化剂或染...
N1-异丙基二乙烯三胺(CAS号:207399-20-0)的市场或研究趋势如何?
随着绿色化学和环保意识的提高,N1-异丙基二乙烯三胺的研究趋势正向低毒、环保的方向发展。市场趋势方面,由于其在功能性材料、药物合成等领域的需求,预计其市场需求将...
4,4-Dimethyl-5,6-dihydro-4H-cyclopenta[d][1,3]thiazol-2-amine(CAS号:1182284-47-4)应用于哪些行业?
该化合物在医药、聚合物、传感器和半导体领域有潜在的应用。在医药领域,作为一种新型的噻唑类化合物,它可能具有抗炎、抗病毒等生物活性。在聚合物领域,该化合物可用作增...
处理5-(PYRIDIN-4-YL)-OXAZOL-2-YLAMINE(CAS号:1014629-83-4)时应注意哪些实验室安全事项?
在处理5-(吡啶-4-基)-2-氧代-1-氧杂环己烷-3-胺时,应佩戴防护眼镜、手套和防护服。实验应在通风橱中进行,以避免吸入有害气体。如果发生泄露,应立即用大...
什么是伊托必利N-氧化物(CAS号:141996-98-7)?
伊托必利N-氧化物是一种化学化合物,其分子结构是伊托必利的N位进行氧化处理后的产物。它具有一定的生物活性,主要用于药物研究和开发。
氟氯烟酸(CAS号:82671-06-5)安全吗?
氟氯烟酸属于有机氯化物,具有一定的毒性,需谨慎处理。在操作过程中,应佩戴防护手套、护目镜和实验服,避免吸入其粉尘或蒸汽。接触皮肤或眼睛可能导致刺激,应采取适当的...
来源期刊
Energy & Environmental Science

Energy & Environmental Science is an international journal dedicated to publishing exceptionally important and high quality, agenda-setting research tackling the key global and societal challenges of ensuring the provision of energy and protecting our environment for the future. The scope is intentionally broad and the journal recognises the complexity of issues and challenges relating to energy conversion and storage, alternative fuel technologies and environmental science. For work to be published it must be linked to the energy-environment nexus and be of significant general interest to our community-spanning readership. All scales of studies and analysis, from impactful fundamental advances, to interdisciplinary research across the (bio)chemical, (bio/geo)physical sciences and chemical engineering disciplines are welcomed. Topics include, but are not limited to, the following: Solar energy conversion and photovoltaics Solar fuels and artificial photosynthesis Fuel cells Hydrogen storage and (bio) hydrogen production Materials for energy systems Capture, storage and fate of CO2, including chemicals and fuels from CO2 Catalysis for a variety of feedstocks (for example, oil, gas, coal, biomass and synthesis gas) Biofuels and biorefineries Materials in extreme environments Environmental impacts of energy technologies Global atmospheric chemistry and climate change as related to energy systems Water-energy nexus Energy systems and networks Globally applicable principles of energy policy and techno-economics














