Article
Chemistry, Organic
Quan Lin, Hegui Gong, Fan Wu
Summary: Here, we present a nickel-catalyzed reductive coupling reaction of bromopyridines with tertiary alkyl bromides, enabling the synthesis of alkylated pyridines bearing an all-carbon quaternary center. This strategy offers mild conditions, a broad substrate scope, and high functional group tolerance. We believe this method provides an alternative solution to the challenging task of synthesizing sterically congested alkylpyridines, benefiting the synthetic community and pharmaceutical industry.
Article
Chemistry, Applied
Sara Payamifar, Foad Kazemi, Babak Kaboudin
Summary: This study introduced a convenient nickel-catalyzed protocol for the Suzuki-Miyaura coupling reaction using a simple mixture of Ni(II) and unfunctionalized beta-cyclodextrin in water. The environmentally friendly and cost-efficient method allows the synthesis of biaryls from arylboronic acids and various aryl halides. The catalyst can be recycled for multiple runs with only a small decrease in catalytic activity.
APPLIED ORGANOMETALLIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Yan-Long Zheng, Pei-Pei Xie, Omid Daneshfar, Kendall N. Houk, Xin Hong, Stephen G. Newman
Summary: A new method has been developed to convert alkyl esters into alkyl ketones, resulting in the synthesis of 65 different alkyl ketones with various functional groups and heterocyclic structures. The study found that catalyst-controlled chemoselectivity could activate the C(acyl)-O bond in the substrate, while density functional theory calculations supported the mechanism of the nickel catalytic cycle.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Biochemistry & Molecular Biology
Huimin Wang, Shuqin Zhang, Minling Xu, Gang Zou
Summary: Researchers have developed a practical and efficient Suzuki coupling reaction of phenols using trans-NiCl(o-Tol)(PCy3)(2)/2PCy(3) as a catalyst and tosyl fluoride as an activator. The compatibility of the nickel catalyst with tosyl fluoride and its fluorosulfate exchange reaction with C-Ar-OH are crucial for the direct use of phenols. Water improves the one-pot reaction significantly, and a variety of electronically and sterically diverse biaryls can be obtained in good yields using 3-10 mol% of the nickel catalyst.
Article
Chemistry, Multidisciplinary
Vincent M. Kassel, Christopher M. Hanneman, Connor P. Delaney, Scott E. Denmark
Summary: Reaction conditions have been developed for refractory heteroaryl-heteroaryl Suzuki-Miyaura cross-couplings using neopentyl heteroarylboronic esters, heteroaryl bromides and chlorides, and potassium trimethylsilanolate (TMSOK) under anhydrous conditions. The addition of trimethyl borate enhances reaction rates by several mechanisms, enabling cross-coupling of diverse reaction partners in good yields and short reaction times.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Chemistry, Organic
Kento Asai, Masahiro Miura, Koji Hirano
Summary: A palladium-catalyzed cross-coupling reaction between diarylmethanol derivatives and diborylmethane has been developed, delivering the corresponding homobenzylic boronates in good yields.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Zahra Khorsandi, Abdol R. Hajipour, Mohamad Reza Sarfjoo, Rajender S. Varma
Summary: The nano-catalytic system described consists of magnetic nanoparticles as the core and edible natural ligands with functional groups as supports for cobalt species. It shows good catalytic activity in C-N cross-coupling reactions and demonstrates excellent efficiency and versatility in an array of coupling reactions. The system is easily accessible and has good recyclability for potential future applications.
Article
Chemistry, Organic
Wen-Xin Li, Bo-Wen Yang, Xuan Ying, Zhuo-Wen Zhang, Xue-Qiang Chu, Xiaocong Zhou, Mengtao Ma, Zhi-Liang Shen
Summary: The direct cross-coupling of diaryl sulfoxides with aryl bromides via C-S bond cleavage was achieved using nickel(II) as the catalyst, 1,2-bis(diphenylphosphino)ethane (dppe) as the ligand, and magnesium turnings as the reducing metal in THF. This reaction showed a wide range of substrates and could be used for gram-scale synthesis. The one-pot reaction is operationally simple and economically efficient.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Physical
Chau Ming So, On Ying Yuen, Shan Shan Ng, Zicong Chen
Summary: This study presents a general chemoselective Suzuki-Miyaura coupling using a Pd/L33 catalyst, showing efficient coupling of polyhalogenated aryl triflates by controlling reactivity order and key factors, achieving high yields and chemoselectivity with low Pd catalyst loading.
Article
Chemistry, Organic
Feiyan Yang, Chuan Wang
Summary: In this study, we employ polycyclic aryl-activated alkyl ammonium triflates as the electrophilic aryl-activated alkylating agent in the nickel-catalyzed hydroxyl- or sulfonamide-directed cross-electrophile coupling reaction with phenyl benzoates, resulting in the synthesis of diverse aryl ketones under mild conditions.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Madasamy Hari Balakrishnan, Madasamy Kanagaraj, Velayudham Sankar, Mahesh Kumar Ravva, Subramaniyan Mannathan
Summary: An efficient palladium-catalyzed denitrogenative Suzuki-Miyaura type cross-coupling reaction was developed for the synthesis of various aryl and alkenyl compounds, including heteroaromatic boronic acids. Additionally, successful application of a reduction reaction was demonstrated to convert ortho-alkenylated products to ortho-alkylated products in high yields.
NEW JOURNAL OF CHEMISTRY
(2021)
Article
Chemistry, Organic
Peng Lei, Yibo Wang, Caixia Zhang, Yuge Hu, Juntao Feng, Zhiqing Ma, Xili Liu, Roman Szostak, Michal Szostak
Summary: In this study, the Sonogashira cross-coupling of aryl ammonium salts was successfully catalyzed by [Pd(NHC)(3-CF3-An)Cl2]. The catalyst exhibited broad scope and excellent C-N activation selectivity. The replacement of pyridine with aniline as an ancillary ligand in the Pd(II)-NHC complex was proven to be highly effective in stabilizing the catalyst.
Article
Chemistry, Physical
Paul O. Peterson, Matthew Joannou, Eric M. Simmons, Steven R. Wisniewski, Junho Kim, Paul J. Chirik
Summary: The synthesis and characterization of phenoxy(imine) iron(II) alkyl precatalysts for C(sp2)-C(sp3) Suzuki-Miyaura cross-coupling reaction is reported. This method utilizes mild alkoxide bases and nonpolar solvents to achieve high efficiency C(sp2)-C(sp3) bond formation with various aryl boronic esters and alkyl bromides. The study also highlights the compatibility of the precatalysts with base-sensitive functionality and the role of boronate intermediates in transmetalation.
Article
Chemistry, Organic
Qianqian Lu, Haixing Guan, Yan-En Wang, Dan Xiong, Tingzhi Lin, Fei Xue, Jianyou Mao
Summary: A visible-light-promoted nickel/photoredox-catalyzed reductive cross-coupling reaction between vinyl bromides and benzyl chlorides has been reported, enabling the synthesis of a diverse array of enantioenriched allylic centers in good yields and high enantioselectivities.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Physical
L. Reginald Mills, David Gygi, Jacob R. Ludwig, Eric M. Simmons, Steven R. Wisniewski, Junho Kim, Paul J. Chirik
Summary: In this study, efficient precatalysts for the C(sp(2))-C(sp(3)) Suzuki-Miyaura cross-coupling reaction between alkyl bromides and neopentylglycol (hetero)arylboronic esters were generated in situ using Cobalt(II) halides in combination with phenoxyimine (FI) ligands. The protocol allowed for efficient C-C bond formation with various nucleophiles and electrophiles. The results also suggested that alkyl radicals play an important role in the catalytic reaction.
