Similar Publications

Iron-Catalyzed Primary Amination of C(sp)-H Bonds.

J Am Chem Soc

September 2024

Department of Biopharmaceutics, West China School of Pharmacy, Sichuan University, Chengdu 610041, China.

Primary amines are privileged molecules in drug development. Yet, there is a noticeable scarcity of methods for directly introducing a primary amine group into the ubiquitous C(sp)-H bonds within organic compounds. Here, we report an iron-based catalytic system that enables direct primary amination of C(sp)-H bonds under aqueous conditions and air.

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Iron-Catalyzed sp C-H Alkylation of Fluorene with Primary and Secondary Alcohols: A Borrowing Hydrogen Approach.

J Org Chem

November 2024

School of Chemical Sciences, National Institute of Science Education and Research (NISER), An OCC of Homi Bhabha National Institute, Bhubaneswar, PO Bhimpur-Padanpur, Via Jatni, District Khurda, Odisha, PIN 752050, India.

The utilization of earth-abundant, cheap, and nontoxic transition metals in important catalytic transformations is essential for sustainable development, and iron has gained significant attention as the most abundant transition metal. A mixture of FeCl (3 mol %), phenanthroline (6 mol %), and KOBu (0.4 eqivalent) was used as an effective catalyst for the sp C-H alkylation of fluorene using alcohol as a nonhazardous alkylating partner, and eco-friendly water was formed as the only byproduct.

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Iron-catalyzed benzylic C-H thiolation photoinduced ligand-to-metal charge-transfer.

Chem Commun (Camb)

May 2024

College of Medicine, Jiaxing University, 118 Jiahang Road, Jiaxing, 314001, P. R. China.

Here, we describe an iron-catalyzed benzylic C-H thiolation of alkylarenes photoinduced ligand-to-metal charge-transfer. The protocol features operational simplicity, mild reaction conditions, and the use of FeCl as catalyst and thiols/disulfides as sulfur sources, which enables the transformation of diverse benzylic C-H bonds into C-S bonds with a high efficiency.

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An oxygen-dependent ligand-controlled chemoselective synthesis of vinyl nitriles and -olefins by coupling a variety of alcohols and benzyl cyanides, catalyzed by a well-characterized, air-stable, easy-to-prepare Fe(II) catalyst () bearing a redox-active arylazo pincer () is reported. The azo-moiety of the ligand backbone acts as an electron and hydrogen reservoir, enabling catalyst to efficiently produce a broad spectrum of vinyl nitriles and -olefins in moderate to good yields selectively under an oxygen and argon atmosphere, respectively.

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Diastereoselective access to ,-glycosyl amino acids iron-catalyzed, auxiliary-enabled MHAT coupling.

Chem Commun (Camb)

March 2024

Laboratoire d'Innovation Moléculaire et Applications (LIMA), UMR 7042, Université de Strasbourg/Université de Haute-Alsace/CNRS, ECPM, 25 rue Becquerel, 67087, Strasbourg, France.

Access to ,-glycosyl amino acids as a novel class of glycomimetics is reported by means of radical generation, intermolecular addition and stereoselective reduction a metal-induced hydrogen atom transfer (MHAT) sequence. The 'matched' coupling of -D-glycals with an enantiopure dehydroalanine bearing a ()-configured benzyl oxazolidinone enables a singular case of two-fold diastereocontrol under iron catalysis. In the common -D-glucal series, the nature of the C-2 substituent was found to play a key role from both reactivity and stereocontrol aspects.

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