Intramolecular C−H Amination of N‐Alkylsulfamides by tert‐Butyl Hypoiodite or N‐Iodosuccinimide

Kiyokawa, Kensuke; Jou, Keisuke; Minakata, Satoshi

doi:10.1002/chem.202102635

Cited by 5 publications

(4 citation statements)

References 75 publications

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“…In 2021, Minakata et al [6] . developed a new reaction based on the intramolecular iodine‐mediated Hofmann‐Löffler‐Freytag (HLF) [7] reaction to construct 1,3‐diamines.…”

Section: Intramolecular 13‐diamination Reactionmentioning

confidence: 99%

“…In 2021, Minakata et al [6] developed a new reaction based on the intramolecular iodine-mediated Hofmann-Löffler-Freytag (HLF) [7] reaction to construct 1,3-diamines. Aminosulfonamides 1 containing benzyl or non-benzyl groups successfully underwent intramolecular oxidative amination by reaction with tertbutyl hypoiodite (t-BuOI) or N-iodosuccinimide (NIS) to produce the cyclic sulfonamides 2.…”

Section: Intramolecular 13-diamination Reactionmentioning

confidence: 99%

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Recent Advances in the Catalytic Synthesis of 1,3‐Diamines

Yang

Wang

2023

ChemCatChem

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1,3‐Diamines are important for many biologically active molecules, but there have been fewer studies on the synthesis of 1,3‐diamines than those on the synthesis of 1,2‐diamines. Relatively speaking, there are not sufficient reports on non‐catalytic methods in this direction. Among various methods, the catalytic construction of diamine products from nitrogen‐containing substrates is the most straightforward, but it suffers from the need to pre‐synthesize nitrogen‐containing substrates and is therefore narrowly used. For non‐specialized substrates, the direct construction of C−N bonds by metal‐ or non‐metal‐catalyzed C−H functionalization is undoubtedly the most efficient approach. This method is currently focused on monofunctionalization, but less has been reported for the simultaneous construction of multiple C−N bonds. Here, we summarize some innovative methods for the synthesis of 1,3‐diamines that have been developed in the past five years, encompassing various directions such as non‐catalytic reaction and metal‐ or non‐metal catalyzed reaction.

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“…In 2021, Minakata et al [6] . developed a new reaction based on the intramolecular iodine‐mediated Hofmann‐Löffler‐Freytag (HLF) [7] reaction to construct 1,3‐diamines.…”

Section: Intramolecular 13‐diamination Reactionmentioning

confidence: 99%

Section: Intramolecular 13-diamination Reactionmentioning

confidence: 99%

Recent Advances in the Catalytic Synthesis of 1,3‐Diamines

Yang

Wang

2023

ChemCatChem

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“…They continued their interest in oxidative amination utilizing iodine as a reagent [240] . Minakata group developed an efficient metal‐free method for synthesising cyclic sulfamides from intramolecular non‐benzylic C−H amination of N ‐alkylsulfamide derivatives by N ‐iodosuccinimide (NIS) or tert ‐butyl hypoiodite (Scheme 120c) [241] …”

Section: C−h Bond Aminationmentioning

confidence: 99%

“…[240] Minakata group developed an efficient metal-free method for synthesising cyclic sulfamides from intramolecular non-benzylic CÀ H amination of N-alkylsulfamide derivatives by N-iodosuccinimide (NIS) or tert-butyl hypoiodite (Scheme 120c). [241] A possible reaction mechanism for intramolecular C(sp 3 )À H bond amination of N-alkylsulfamides was proposed (Scheme 121). The reaction mechanism was initiated by the hydrogen-iodine exchange between t-BuOI and N-alkylsulfa-…”

Section: -Catalyzed/mediated C(sp 3 )à H Aminationmentioning

confidence: 99%

Cross‐Coupling of C−H and N−H Bonds: A Hydrogen Evolution Strategy for the Construction of C−N Bonds

et al. 2022

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The progress in CÀ N bond construction is significant in synthetic and biological chemistry. Cross-dehydrogenative couplings of CÀ H and NÀ H motifs serve as a unique class of the most atom-economical and straightforward strategies for constructing CÀ N bonds. Herein, we enclosed the most updated methodologies developed in the assembly of CÀ N bonds via photo-catalyzed, transition-metal-catalyzed, electrochemical, and metal-free amination and amidation reactions of saturated and unsaturated CÀ H bonds. Compared with the well-established transition-metal-catalyzed protocols, electricity, or visible light-mediated amination and amidation reactions are competent and appealing. Plausible mechanistic pathways are also described in representative amidation and amination reactions to provide insights for the future development of environmentally kind processes.

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Gold(I)−Catalyzed Synthesis of Cyclic Sulfamides via an Intramolecular Dehydrative Amination of Allylic Alcohols: A Strategy for 1,3‐Diamine Synthesis

Lee,

Kim,

Ryu

2024

Adv Synth Catal

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A novel gold(I)‐catalyzed intramolecular dehydrative amination method has been developed to synthesize diverse cyclic sulfamides efficiently. Reactions proceed smoothly at room temperature using a combination of (IPr)AuCl (5 mol%) and AgBF4 (5 mol%). This method showcases a broad substrate scope, encompassing challenging seven‐membered ring structures, and exhibits functional group compatibility. Moreover, the reaction demonstrates high stereoselectivity, allowing the synthesis of enantiomerically enriched cyclic sulfamides from chiral secondary allylic alcohols. The synthesized cyclic sulfamides serve as valuable intermediates for generating 1,3‐diamines. This approach provides an improved route for cyclic sulfamide synthesis and a strategic entry point for obtaining essential 1,3‐diamine derivatives.

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Intramolecular C−H Amination of N‐Alkylsulfamides by tert‐Butyl Hypoiodite or N‐Iodosuccinimide

Cited by 5 publications

References 75 publications

Recent Advances in the Catalytic Synthesis of 1,3‐Diamines

Recent Advances in the Catalytic Synthesis of 1,3‐Diamines

Cross‐Coupling of C−H and N−H Bonds: A Hydrogen Evolution Strategy for the Construction of C−N Bonds

Gold(I)−Catalyzed Synthesis of Cyclic Sulfamides via an Intramolecular Dehydrative Amination of Allylic Alcohols: A Strategy for 1,3‐Diamine Synthesis

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