- Aerobic Copper-Catalyzed Salicylaldehydic Cformyl?H Arylations with Arylboronic Acids
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We report a challenging copper-catalyzed Cformyl?H arylation of salicylaldehydes with arylboronic acids that involves unique salicylaldehydic copper species that differ from reported salicylaldehydic rhodacycles and palladacycles. This protocol has high chemoselectivity for the Cformyl?H bond compared to the phenolic O?H bond involving copper catalysis under high reaction temperatures. This approach is compatible with a wide range of salicylaldehyde and arylboronic acid substrates, including estrone and carbazole derivatives, which leads to the corresponding arylation products. Mechanistic studies show that the 2-hydroxy group of the salicylaldehyde substrate triggers the formation of salicylaldehydic copper complexes through a CuI/CuII/CuIII catalytic cycle.
- Xiao, Lin,Lang, Tao-Tao,Jiang, Ying,Zang, Zhong-Lin,Zhou, Cheng-He,Cai, Gui-Xin
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supporting information
p. 3278 - 3283
(2021/02/01)
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- Deoxygenative Arylation of Carboxylic Acids by Aryl Migration
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An unprecedented deoxygenative arylation of aromatic carboxylic acids has been achieved, allowing the construction of an enhanced library of unsymmetrical diaryl ketones. The synergistic photoredox catalysis and phosphoranyl radical chemistry allows for precise cleavage of a stronger C?O bond and formation of a weaker C?C bond by 1,5-aryl migration under mild reaction conditions. This new protocol is independent of substrate redox-potential, electronic, and substituent effects. It affords a general and promising access to 60 examples of synthetically versatile o-amino and o-hydroxy diaryl ketones under redox-neutral conditions. Furthermore, it also brings one concise route to the total synthesis of quinolone alkaloid, (±)-yaequinolone A2, and a viridicatin derivative in satisfying yields.
- Ruzi, Rehanguli,Ma, Junyang,Yuan, Xiang-Ai,Wang, Wenliang,Wang, Shanshan,Zhang, Muliang,Dai, Jie,Xie, Jin,Zhu, Chengjian
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p. 12724 - 12729
(2019/11/05)
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- ECO-FRIENDLY MATERIALS AND METHODS FOR RENEWABLE AND SUSTAINABLE APPLICATIONS IN MATERIAL CHEMISTRY
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The invention relates to novel hydrazide-based templates, methods of making the same, and methods of using the hydrazide-based templates as molecular scaffolds for asymmetric light driven transformations, light driven material synthesis, and biological applications. Furthermore, the present invention relates to photoinitiators, monomers, and polymers derived from biomass, together with methods and methods of using the same.
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Page/Page column 42
(2017/09/27)
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- Rh(III)-catalyzed aldehyde C-H bond functionalization of salicylaldehydes with arylboronic acids
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A Rh(III)-catalyzed aldehyde C-H bond functionalization of salicylaldehydes with arylboronic acids has been developed, with features of mild reaction condition and high efficiency. Furthermore, the functionalized 2-hydroxybenzophenone could be subject to divergent synthesis of heterocycles.
- Wang, Dahai,Cui, Sunliang
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p. 8511 - 8516
(2016/01/25)
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- Benzofurans from benzophenones and dimethylacetamide: Copper-promoted cascade formation of furan O1-C2 and C2-C3 bonds under oxidative conditions
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DMA donates: Copper(II) acetate and 8-hydroxyquinoline promote the formation of a benzofuran core through a cascade of copper-catalyzed processes wherein the key carbon atom comes from the dimethylacetamide (DMA) solvent. Strong evidence for the participation of a Wacker cyclization catalyzed solely by copper is provided, not only in the title reaction from benzophenones but also from 2-hydroxy-α-arylstyrene derivatives. Copyright
- Moure, Maria J.,Sanmartin, Raul,Dominguez, Esther
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supporting information; experimental part
p. 3220 - 3224
(2012/05/05)
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- Direct C-H bond arylation of 2-hydroxybenzaldehydes with arylboronic acids via ligand-free palladium catalysis
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A mild and efficient ligand-free palladium-catalyzed direct C-H bond arylation reaction was developed to afford 2-hydroxybenzophenones in good to excellent yields from easily available 2-hydroxybenzaldehydes and arylboronic acids. The given reaction provided one of the easiest pathways for accessing 2-hydroxybenzophenones, and a variety of functional groups could be tolerated in this process.
- Weng, Fei,Wang, Chengming,Xu, Bin
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supporting information; experimental part
p. 2593 - 2596
(2010/07/04)
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- Synthesis of 2,3-disubstituted benzofurans from ortho-acylphenols
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2,3-Disubstituted benzofuran derivatives were synthesized from ortho-acylphenols in two steps. The β-aryloxyacrylates prepared from the ortho-acylphenols were treated with n-Bu3SnH/ AIBN and then with 5% HCl-EtOH to afford 2,3-disubstituted benzofurans. Georg Thieme Verlag Stuttgart.
- Kim, Kwang-Ok,Tae, Jinsung
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p. 387 - 390
(2007/10/03)
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- Palladium-catalyzed coupling reaction of salicylaldehydes with aryl iodides via cleavage of the aldehyde C-H bond
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It has been found that the cross-coupling reaction of salicylaldehydes with aryl iodides smoothly proceeds by using a catalyst system of PdCl2/LiCl in the presence of Na2CO3 as base to give the corresponding 2-aroylphenols in good yields, which appears to involve cleavage of the aldehyde C-H bond.
- Satoh, Tetsuya,Itaya, Tomoaki,Miura, Masahiro,Nomura, Masakatsu
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p. 823 - 824
(2007/10/03)
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