Article
Chemistry, Organic
Jin-He Na, Xiang Liu, Jia-Wen Jing, Jing Wang, Xue-Qiang Chu, Mengtao Ma, Hao Xu, Xiaocong Zhou, Zhi-Liang Shen
Summary: A step-economical and efficient one-pot reaction was developed for the direct cross-coupling of aryl fluorosulfate with aryl bromide. This reaction, conducted at room temperature in THF solvent, does not require the use of preprepared/commercial organometallic reagents. By utilizing nickel catalyst, magnesium turnings, and lithium chloride, the desired biaryls were obtained in moderate to good yields with reasonable functional group compatibility.
Article
Chemistry, Multidisciplinary
Giuseppe Dilauro, Francesco Messa, Fabio Bona, Serena Perrone, Antonio Salomone
Summary: A simple cobalt complex, Co(phen)Cl₂, has been found to be a highly efficient and cost-effective precatalyst for various cross-coupling reactions involving aromatic and aliphatic organoaluminum reagents with aryl, heteroaryl, and alkyl bromides. New C(sp²)-C(sp²) and C(sp²)-C(sp³) bonds can be formed in good to excellent yields and high chemoselectivity under mild reaction conditions.
CHEMICAL COMMUNICATIONS
(2021)
Article
Chemistry, Organic
Chuntao Zhong, Mengna Liu, Xianchao Qiu, Hao Wei, Benqiang Cui, Yanhui Shi, Changsheng Cao
Summary: A nickel-catalyzed cross-coupling reaction between aryl methyl sulfides and aryl bromides has been developed to efficiently access biaryls. The method has a wide scope of substrates and is scalable, with commercially available aryl bromides being used without the need for preparation of organometallic reagents. This reaction has high application value.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Ruofei Cheng, Graham de Ruiter, Chao-Jun Li
Summary: Cobalt-based catalysts have shown unique advantages in cross-coupling reactions, with higher catalytic activity and lower toxicity compared to palladium and nickel catalysts. A novel cobalt-catalyzed alkyl-alkyl cross-coupling reaction of hydrazone with alkyl halides has been developed under mild reaction conditions, using a PNP-type pincer ligand as an essential catalyst. Both aldehyde and ketone hydrazones are compatible with this reaction, producing a series of C(sp(3))-C(sp(3)) coupling products in moderate to good yields.
CHEMICAL COMMUNICATIONS
(2022)
Article
Multidisciplinary Sciences
Eiji Shirakawa, Yuki Ota, Kyohei Yonekura, Keisho Okura, Sahiro Mizusawa, Sujan Kumar Sarkar, Manabu Abe
Summary: An electron has been found to catalyze the cross-coupling reaction of organometallic compounds with aryl halides, which is more desirable for green and sustainable chemistry compared to transition metal catalysis. However, high temperature is required for this electron catalysis. We discovered that visible light photoirradiation can accelerate the electron-catalyzed reaction by using photoredox catalysis, enabling the reaction to proceed at room temperature. The supply of the electron catalyst through photoredox catalysis also expands the scope of aryl halides.
Article
Chemistry, Organic
Hao Xu, Cai-Yu He, Bo-Jie Huo, Jia-Wen Jing, Chengping Miao, Weidong Rao, Xue-Qiang Chu, Xiaocong Zhou, Zhi-Liang Shen
Summary: In this study, a cross-electrophile coupling of aryl thiols with aryl bromides was reported, where C-S bond activation occurred instead of S-H bond cleavage, leading to the formation of thioethers as the major products. The reaction proceeded effectively with a nickel catalyst, magnesium turnings, and lithium chloride in THF at room temperature, and a variety of structurally diverse biaryls were obtained in moderate to good yields.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Letter
Chemistry, Organic
Panchi Guo, Hao Jin, Jinhui Han, Liang Xu, Pengfei Li, Miao Zhan
Summary: This study demonstrates a nickel-catalyzed Negishi cross-coupling reaction for the synthesis of versatile organoboron products with high functional-group tolerance. The reaction allows for the coupling of unactivated tertiary alkyl electrophiles with boron-stabilized organozinc reagents. The importance of the Bpin group in accessing the quaternary carbon center is highlighted, and the practicality of the prepared quaternary organoboronates is showcased through their conversion to other useful compounds.
Article
Chemistry, Organic
Chenchen Li, Qi Qin, Aocong Guan, Wen Yang, Wanxiang Zhao
Summary: We present a general and efficient transition-metal-free C-C bond cross-coupling reaction of (hetero)-aryl ethers and diarylmethanes via C-(sp(2))-O bond cleavage. The coupling reactions mediated by KHMDS demonstrated high efficiency, broad substrate scope, and good functional group tolerance. The robustness and practicality of this protocol were further demonstrated by gram-scale preparation and diversified product derivatization.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Xuejing Peng, Jingxian Huang, Guan-Yu Han, Xing-Zhong Shu
Summary: In this manuscript, a dynamic kinetic cross-electrophile coupling reaction of benzylic alcohols with alkenyl triflates is reported. This method allows for the replacement of the alcohol group with an alkenyl functionality, resulting in versatile benzyl-substituted cyclic alkenes. The reaction is orthogonal to existing reductive coupling methodologies and tolerates various functional groups.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Multidisciplinary
Miao Wang, On Ying Yuen, Chau Ming So
Summary: This paper presents the first examples of palladium-catalyzed desulfinative cross-coupling reaction of polyhalogenated aryl triflates with aryl sulfinate salts. The catalyst system exhibited excellent reactivity and chemoselectivity in this reaction, which had a wide substrate scope and provided a simple method for constructing functionalized biaryl motifs. The interaction between the indolyl phosphine ligand and the Pd center played a key role in the reactivity and chemoselectivity of this reaction.
CHINESE JOURNAL OF CHEMISTRY
(2023)
Letter
Chemistry, Organic
Na-Na Ma, Xuan-Bo Hu, Yuan-Shuai Wu, Ya-Wen Zheng, Mengtao Ma, Xue-Qiang Chu, Hao Xu, Haiqing Luo, Zhi-Liang Shen
Summary: A direct cross-coupling reaction of aryl thioether with aryl bromide was successfully achieved using nickel salt, magnesium, and lithium chloride as catalysts in tetrahydrofuran solvent at room temperature. The one-pot reactions efficiently cleaved the C-S bond, yielding the desired biaryls in moderate to good yields, without the need for pregenerated or commercial organometallic reagents.
Article
Chemistry, Organic
Peter G. N. Neate, Bufan Zhang, Jessica Conforti, William W. Brennessel, Michael L. Neidig
Summary: Dilithium amides have been developed as a bespoke and general ligand for iron-catalyzed Kumada-Tamao-Corriu cross-coupling reactions, allowing for diverse coupling reactions without significant modification of the catalytic protocol. This represents a rare example of a single iron-catalyzed system effective across various coupling reactions while remaining operationally simple.
Article
Chemistry, Organic
Regina M. Oechsner, Ivo H. Lindenmaier, Ivana Fleischer
Summary: We present a nickel catalyzed C-S cross-coupling reaction of aryl and alkenyl triflates with alkyl thiols. By using an air-stable nickel precatalyst, various thioethers could be synthesized under mild reaction conditions within a short reaction time. The reaction demonstrated a broad substrate scope, including pharmaceutically relevant compounds.
Article
Chemistry, Organic
Ikuya Fujii, Kazuhiko Semba, Yoshiaki Nakao
Summary: Rhodium-aluminum bimetallic complexes catalyze the Kumada-Tamao-Corriu (KTC) cross-coupling reaction using arylmagnesium compounds generated from corresponding aryl fluorides or chlorides. This method allows the challenging KTC coupling reaction to be carried out using aryl fluorides as nucleophiles, resulting in various biaryls.
Article
Chemistry, Inorganic & Nuclear
Fei Fan, Lixing Zhao, Meiming Luo, Xiaoming Zeng
Summary: Chemically inert C(aryl)-F bonds have been successfully cleaved and coupled with unreactive C(aryl)-O bonds using chromium catalysis, enabling high selectivity and efficiency for cross-electrophile coupling.
