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Journal of Organic Chemistry
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#1Jordan Neale Smith (MacDiarmid Institute for Advanced Materials and Nanotechnology)H-Index: 1
#2Thomasin K. Brind (MacDiarmid Institute for Advanced Materials and Nanotechnology)
Last. Nigel T. Lucas (MacDiarmid Institute for Advanced Materials and Nanotechnology)H-Index: 20
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The three-component reaction between a resorcinol, 1,3-dimethoxybenzene, and an alkyl aldehyde (R = C1–C11) along with BF3·OEt2 affords a C2v-symmetric resorcin[4]arene tetraether in one step; in m...
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#1Sha Hu (Fudan University)H-Index: 1
#2Jiaqi Wang (Fudan University)
Last. Fen-Er Chen (Fudan University)H-Index: 22
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An organocatalytic asymmetric enantioselective domino oxa-Michael-Mannich-[1,3]-amino rearrangement reaction of N-tosylsalicylimines with a wide range of α,β-unsaturated aldehydes utilizing diaryprolinol silyl ethers catalysis is described. The catalytic reactions proceed with excellent enantioselectivity (up to 99% ee) to produce the corresponding chair N-tosylimines-chromenes with a yield up to 99%, tolerating a range of functional groups. This methodology offers a new method with great potent...
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#1Ji-tian LiuH-Index: 6
Last. Xiaoxun LiH-Index: 13
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x-membered lactams were synthesized via either an amidation of sp3 C–H bonds or an electrophilic substitution of arenes via Ir-nitrene intermediates. With the employment of a readily available irid...
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#1Guangfan Zheng (SNNU: Shaanxi Normal University)H-Index: 5
#2Xujing Duan (SNNU: Shaanxi Normal University)
Last. Xingwei Li (SNNU: Shaanxi Normal University)H-Index: 52
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Reported herein is Rh(III)-catalyzed annulation of N-unprotected 2-arylindols with quinone monoacetals for straightforward synthesis of [4,3,1]-bridged carbocycles with exclusive C(3)-selectivity. Mechanistic studies, particularly deuterium labeling experiments, suggest that the coupling likely proceeds via twofold C-H activation with twofold migratory insertion into the enone mioeties
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Evaluation of the hemilability of hybrid ligands provides a key to understand the metal-ligand cooperation in transition metal catalysis. Here, we design and synthesize a type of RuII complexes based on the hemilability of N-heterocyclic carbenes (NHCs), pyridine, and pyrazole, to compare their activity with other reported Ru catalysts in benzylic C-H oxidation. The RuII catalysts showed ultrastrong catalytic activity in water at room temperature and achieved a turnover frequency (TOF) = 114 h-1...
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Manipulating frontier orbital energies of aromatic molecules with substituents is key to a variety of chemical and material applications. Here, we investigate a simple strategy for achieving high-energy in-plane orbitals for aromatics simply by positioning iodine atoms next to each other. The lone pair orbitals on the iodines mix to give a high-energy in-plane σ-antibonding orbital as the HOMO. We show that this effect can be used to manipulate orbital gaps, the symmetry of the highest occupied ...
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A unified and concise first asymmetric total syntheses of (−)-citreoisocoumarin (2), (−)-citreoisocoumarinol (3), 12-epi-citreoisocoumarinol (4), (−)-mucorisocoumarins A (5) and B (6) have been accomplished from the common intermediate 1. Central to the synthetic approach is a regioselective gold(I)-catalyzed 6-endo-dig cyclization strategy for the construction of isocoumarin skeleton. The other key steps in this approach included Sonogashira coupling, Tsuji-Wacker oxidation, Evans-Saksena’s 1,3...
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An efficient method for the synthesis of diverse 1,3-diarylpyrazoles via consecutive aryne generation has been developed. The bisaryne precursors bearing o-iodo- and o-silylaryl triflate moieties were prepared by sequential Suzuki–Miyaura and Chan–Lam–Evans cross-coupling reactions. The selective generation of the first aryne triggered by a silylmethyl Grignard reagent followed by the second aryne generation mediated by a fluoride ion allowed for the synthesis of diverse multisubstituted 1,3-dia...
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#1Yan-Jun Zhuang (USTC: University of Science and Technology of China)
Last. Yan-Biao Kang (USTC: University of Science and Technology of China)H-Index: 18
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Salicylaldehyde is established as an efficient visible light photocatalyst for the first time. Compared to other simple aldehyde analogies, salic-ylaldehyde has a unique deprotonative red-shift from 324 nm to 417 nm and gives rise to the remarkable increase of fluorescence quantum from 0.0368 to 0.4632, thus enables salicylaldehyde as a visible light (> 400 nm) photocatalyst. The experimental investigations suggest that the reactive radical species are generated by sensitization of the substrate...
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