Article
Chemistry, Organic
Lei Dai, Qiuyu Yu, Jinghang Zhang, Fan Wu, Chang Wang, Jinpeng Zhang, Liangce Rong
Summary: An efficient electrochemical radical delta-H sulfonylation reaction of para-quinone methides and sodium sulfinates has been achieved under common laboratory conditions. The reaction allows for the construction of a new C(sp(2))-S bond to synthesize 4-((aryl,arylsulfonyl)methylene)-2,5-cyclohexadiene derivatives with a broad substrate scope and good functional group tolerance. Further studies have shown that the reaction exhibits excellent regional selectivity.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Sajjad Ahmed, Mohammad Yaqoob Bhat, Feroze Hussain, Qazi Naveed Ahmed
Summary: In this study, the activation of diphenyl phosphite by BF3/BF4(-) resulted in the formation of thionium ions from aldehydes and thiophenols. These reactive species then reacted with in situ generated phenol, leading to the synthesis of diarylmethyl thioethers. It was found that the addition of external phenol in the reaction yielded unsymmetrical gem-diarylmethyl thioethers in good yields.
Article
Chemistry, Organic
Sabrina Giofre, Manfred Keller, Leonardo Lo Presti, Egle M. Beccalli, Letizia Molteni
Summary: The study demonstrates that the Pd(II)-catalyzed reaction of N-allyl-2-aminophenols can lead to different pathways and products under different conditions, with the oxidant playing a key role in the reaction.
Article
Chemistry, Organic
Wen-Dao Chu, Tian -Tian Liang, Hao Ni, Zhi-Hong Dong, Zhihui Shao, Yong Liu, Cheng-Yu He, Ruopeng Bai, Quan-Zhong Liu
Summary: In this study, we describe a Pd(0)-catalyzed intermolecular asymmetric dearomative [3 + 2] annulation of phenols with vinyl cyclopropanes through the in situ generation of ortho-quinone methide intermediates. Highly functionalized spiro-[5,6] bicycles with three contiguous stereogenic centers, including an all-carbon quaternary, were obtained with excellent stereoselectivities. Density functional theory (DFT) calculations suggest that the reactions are controlled by thermodynamics.
Article
Chemistry, Organic
Jing Wang, Tingting Wang, Hongguang Du, Ning Chen, Jiaxi Xu, Zhanhui Yang
Summary: An iridium-catalyzed and phenol-directed deoxygenation method is described for the synthesis of 4-alkylphenols, which offers low catalyst loading, high functionality compatibility, and excellent site-selectivity. The applications in late-stage modification of steroids and gram-scale total synthesis of a Gastrodia elata extract are also highlighted. Mechanistically, the interemediacy of quinone methide controls the site-selectivity, and the formation of iridium hydride serves as the rate-limiting step.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Laura Burchill, Aaron J. Day, Oussama Yahiaoui, Jonathan H. George
Summary: Total synthesis of the Rhododendron meroterpenoids rubiginosins A and G, which possess unusual 6-6-6-4 ring systems, has been achieved using a bioinspired cascade approach. Stepwise synthesis of these natural products, and the related 6-6-5-4 meroterpenoids fastinoid B and rhodonoid B, from naturally occurring chromene precursors is also reported.
Review
Chemistry, Applied
Zhibin Yue, Fang Fang, Yan Xia, Pengfei Li, Wenjun Li
Summary: Conjugate addition is a powerful method in organic synthesis for forming carbon-carbon and carbon-heteroatom bonds. Advances in asymmetric conjugate addition have been made with the development of asymmetric catalysis, but controlling selectivity becomes a challenge in extended conjugated systems.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Organic
Yixin Jia, Jiaolong Meng, Deqing Hu, Hao Kang, Xuefeng Jiang
Summary: Aerobic oxidation of organoboron was achieved via uranyl photocatalysis using the principle of indirect single electron transfer. Multiple phenols and alcohols, including natural products and pharmaceuticals, were obtained under mild ambient conditions. The i-SET process between the uranyl catalyst and triethylamine was determined, and oxygen was confirmed to be derived from O-2 through O-18 labeling experiments.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Applied
Guan-Nan Li, Hao-Cong Li, Meng-Ru Wang, Zhan Lu, Bing Yu
Summary: A visible-light-induced acylation aromatization reaction of para-quinone methides to access alpha,alpha'-diarylated ketones using cheap and readily available carboxylic acids as acylating reagents via deoxygenation was developed. The method offers a simple and efficient approach to synthesis and shows a broad substrate scope, allowing for late-stage functionalization of drug molecules.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Organic
Shiqi Jia, Wenling Qin, Pengfei Wang, Hailong Yan
Summary: An organocatalytic methodology has been developed for the construction of axially chiral nonsymmetric biaryltriols with high efficiency and selectivity. The synthesized biaryltriols can be used as chiral ligands for preparing chiral sec-alcohols and as organocatalysts for asymmetric Petasis reactions. Additionally, they show potential as selective fluorescent sensors for Ru3+ ions.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Organic
Biquan Xiong, Wenli Shang, Weifeng Xu, Yu Liu, Ke-Wen Tang, Wai-Yeung Wong
Summary: A facile and efficient method for the synthesis of alpha-diarylmethyl substituted phenols has been developed using phosphoric acid as the catalyst and water as the green solvent. Addition of TEMPO as an additive allows for the generation of diaryl-substituted para-quinone methides. These reactions exhibit high functional group tolerance, good to excellent yields, and unique selectivity, providing a new method for organic synthesis.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Applied
Yunying Yan, Haiqiong Li, Fenfen Xie, Wenhua Lu, Zhengbing Zhang, Linhai Jing, Pan Han
Summary: Here, electrochemical reductive carboxylation of para-quinone methides with CO2 was developed, enabling the synthesis of various value-added carboxylic acids in moderate to excellent yields. This protocol features high atom economy and environmental friendliness.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Physical
Guosong Shen, Faqian He, Wansen Xie, Huanchao Gu, Xiaoyu Yang
Summary: Asymmetric diastereodivergent catalysis is an important strategy for accessing different stereoisomers of a molecule. In this study, a new method for the asymmetric diastereodivergent synthesis of chromanes with C2,C3-contiguous tetrasubstituted stereocenters was reported using chiral phosphoric acid catalysts.
Article
Agriculture, Multidisciplinary
Danielle da Silva Eugenio, Kelem Silva Fonseca, Ariel Sharon de Araujo Nogueira Marcelino, Valecia Nogueira Santos e Silva, Sergio Luiz Ferreira-Silva, Aurelio Paes Barros-Junior, Flavio Pereira da Mota Silveira, Welder de Araujo Rangel Lopes, Hugo Rafael Bentzen Santos, Adriano do Nascimento Simoes
Summary: This study demonstrates that increased phosphorus supply in the soil can lead to higher phosphorus content in cassava roots and stems, as well as increased phenylpropanoid metabolism and enzyme activity, enhancing the antioxidant capacity of cassava.
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY
(2021)
Article
Chemistry, Organic
Hui Gao, Xinyu Chen, Pei-Long Wang, Meng-Meng Shi, Ling-Long Shang, Heng-Yi Guo, Hongji Li, Pinhua Li
Summary: A catalyst-free and oxidant-free electrochemical C-H arylation method has been developed for xanthenes and thioxanthenes, yielding various cross-coupling products in moderate to good yields. This atom- and step-economical approach utilizes affordable and readily available arenes and heteroarenes as direct partners, enabling C(sp(2))-H/C(sp(3))-H type reactions.
ORGANIC CHEMISTRY FRONTIERS
(2022)
