Article
Chemistry, Multidisciplinary
Zi-Tong Pan, Li-Miao Shen, Fentahun Wondu Dagnaw, Jian-Ji Zhong, Jing-Xin Jian, Qing-Xiao Tong
Summary: An efficient Minisci reaction of heteroarenes and unactivated C(sp(3))-H alkanes was achieved using inexpensive FeCl3 as a photocatalyst. The photogenerated chlorine radical participated in the hydrogen atom transfer of C-H, thereby initiating this reaction. Surprisingly, salt water and even seawater can serve as a chlorine radical source, offering an enlightening idea for future organic synthesis methods.
CHEMICAL COMMUNICATIONS
(2023)
Article
Chemistry, Organic
David T. Mooney, Peter R. Moore, Ai-Lan Lee
Summary: A new method has been developed for the direct C-H carboxyamidation of purines, allowing for the installation of primary, secondary, and tertiary amides. This metal-free and affordable approach is operationally simple and suitable for late-stage functionalizations of biologically important molecules.
Article
Chemistry, Physical
Yong-Liang Su, Geng-Xin Liu, Luca De Angelis, Ru He, Ammar Al-Sayyed, Kirk S. Schanze, Wen-Hao Hu, Huang Qiu, Michael P. Doyle
Summary: This study demonstrates the efficient generation of functionalized derivatives through photocatalyzed multicomponent reactions using nitrogen aromatic heterocycles, alkenes, and diazo compounds. The reaction shows high functional group tolerance and exacting regioselectivities. Mechanistic studies, including photophysical measurements, provide insights into this radical cascade reaction.
Article
Chemistry, Organic
Chaodong Wang, Shengjie Song, Zhi Chen, Dengjian Shen, Zhenhui Wang, Jiadi Zhou, Jingjing Guo, Jianjun Li
Summary: In this study, a visible-light-triggered photocatalyst-free radical cascade Minisci reaction was developed for the synthesis of diverse fi-C(sp3) heteroarylated alcohols/ethers using heteroarenes, alkenes, and water/alcohols. This protocol is mild, scalable, and demonstrates broad substrate scope and functional group tolerance. Mechanistic studies reveal that heteroarenes can serve as photocatalysts for single-electron transfer with persulfate.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Medicinal
James J. Perkins, Valerie W. Shurtleff, Alayna M. Johnson, Abdellatif El Marrouni
Summary: This study presents a strategy for functionalizing purine nucleosides through photoredox and nickel-catalyzed sp(2)-sp(3) cross-coupling, allowing for coupling of unprotected nucleosides with readily available alkyl bromides, providing opportunities for their application in parallel medicinal chemistry.
ACS MEDICINAL CHEMISTRY LETTERS
(2021)
Article
Chemistry, Organic
Gang Liu, Xianfeng Mu, Miao Tian, Weili Wang, Chunhui Zou, Yiwen Chen, Mingwu Yu
Summary: We developed a radical deoxy-functionalization strategy for direct C-H alkylation of purines and purine nucleosides with alcohols under blue LED irradiation. The reaction exhibited high regioselectivity and broad functional group tolerance. It provided a wide range of products in good yields, avoiding the use of transition metal catalysts and organometallic reagents.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Review
Chemistry, Multidisciplinary
Felix Kaspar, M. Rhia L. Stone, Peter Neubauer, Anke Kurreck
Summary: Nucleosides and their analogs are fundamental biomolecules in life science, but current synthetic methods are generally laborious and inefficient. Shorter routes with fewer protecting groups show better sustainability. Future efforts should focus on non-chromatographic purification steps, shorter routes, and higher substrate loading for more efficient nucleoside synthesis.
Article
Chemistry, Multidisciplinary
Saira Hafeez, Aamer Saeed
Summary: Visible light-induced acylation of heteroaromatic compounds is achieved using benzoyl hydrazides as an efficient acyl source under mild reaction conditions. The photo-redox catalyzed oxidative cleavage of hydrazides leads to in situ formation of acyl radicals, which subsequently couple with various N-heterocycles to produce acylated products. This synthetic strategy performs the classic Minisci reaction in an eco-friendly and greener way with functional group tolerance and regioselectivity. Control experiments confirm the radical pathway for this transformation.
Article
Chemistry, Multidisciplinary
Nian Xu, Maoping Pu, Han Yu, Gaofei Yang, Xiaohua Liu, Xiaoming Feng
Summary: This study achieved the direct alpha-alkylation of acyclic carbonyls with nonactivated hydrocarbons using iron-based catalysts, resulting in highly selective products. The use of a chiral iron complex and oxidants allowed for the high enantioselectivity (up to 99% ee) with good compatibility in yields (up to 88%).
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Vincent L. Revil-Baudard, Samir Z. Zard
Summary: A new reaction was discovered for modifying alkenes and heteroarenes, particularly in biologically active substances. The saponification of acetate produces fluorocyclobutanes, which could lead to new drug candidates with potential therapeutic effects.
HELVETICA CHIMICA ACTA
(2021)
Article
Chemistry, Multidisciplinary
Hari K. Akula, Suyeal Bae, Padmanava Pradhan, Lijia Yang, Barbara Zajc, Mahesh K. Lakshman
Summary: The underexploited potential of N-unprotected 8-formyl derivatives of adenosine and 2'-deoxyadenosine for C8 modifications of these nucleosides is discussed in this study. The researchers report the straightforward and scalable synthesis of N-unprotected 8-formyladenine nucleoside derivatives, and demonstrate their versatility for C8 diversification through various reactions.
CHEMICAL COMMUNICATIONS
(2022)
Article
Chemistry, Applied
Xinxin Wang, Xin Shao, Zhu Cao, Xinxin Wu, Chen Zhu
Summary: A metal-free deformylative Minisci-type reaction is developed using aliphatic aldehydes as alkyl radical precursors. The reaction proceeds through a sequence of hydrogen atom abstraction (HAA) from the aldehyde and decarbonylation under mild photochemical conditions. It offers advantages such as good regioselectivity, broad substrate scope, and easy operation. The reaction is also suitable for late-stage functionalization of complex heteroarenes and can be easily scaled up.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Organic
Chao Xia, Dongchao Wang, Haiming Guo
Summary: Efficient alkylation of purines with ortho-hydroxybenzyl alcohols under mild condition has been achieved by Sc(OTf)(3) catalysis, leading to the formation of various acyclic nucleoside analogs with excellent yields of up to 96% and maintained yields as reactions were scaled up.
CHINESE JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Marin Kemmochi, Yusuke Miyamoto, Yuto Sumida, Hirohisa Ohmiya
Summary: The photoexcitable borate enables Minisci C-H alkylation of heteroarenes, providing a clean system using alkylborate, O-2, and visible light. Direct photoexcitation of alkylborate generates tertiary, secondary, and primary-alkyl radicals, including methyl radicals, offering a choice for the functionalization of heteroarenes.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Francisco Jose Aguilar Troyano, Khadijah Anwar, Fabian Mohr, Guillaume Robert, Adrian Gomez-Suarez
Summary: In this study, a simple strategy for synthesizing fused heterocycles through a deoxygenative, intramolecular Minisci-type reaction is presented. This method allows for the generation of complex polycyclic scaffolds in just three steps using easily accessible starting materials such as chlorinated heteroarenes and 1,3-diols. By using saccharide derivatives as the starting 1,3-diol motif, novel heterocyclic scaffolds with excellent diastereoselectivity and formal retention of configuration at the newly formed C -C bond can be obtained.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
