Transition Metal Catalyzed Azidation Reactions

Sala, Roberto; Loro, Camilla; Foschi, Francesca; Broggini, Gianluigi

doi:10.3390/catal10101173

Cited by 22 publications

(7 citation statements)

References 152 publications

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“…Regarding C–H azidation of anilines, a limited number of literature precedents were available in comparison with aliphatic couterparts (Scheme ). Jiao et al reported a pioneering work on copper-catalyzed C–H azidation employing CuBr and TBHP .…”

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confidence: 99%

Regioselective C–H Azidation of Anilines and Application to Synthesis of Key Intermediate for Pharmaceutical

Shimada

Takahashi

2021

J. Org. Chem.

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A catalytic system for regioselective C−H azidation of inactive anilines was developed. In the presence of CuSO 4 •5H 2 O, simultaneous addition of NaN 3 and Na 2 S 2 O 8 to aq. CH 3 CN solution of free anilines under weakly acidic conditions (pH 4.5) smoothly underwent C−H azidation to provide corresponding α-azidated products in high yields. Methyl αazidoanthranilate obtained by this method was readily transformed via simple reduction followed by cyclization to methyl 2-ethoxybenzimidazol-7carboxylate, a key intermediate for antihypertensive Candesartan Cilexetil.

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confidence: 99%

Regioselective C–H Azidation of Anilines and Application to Synthesis of Key Intermediate for Pharmaceutical

Shimada

Takahashi

2021

J. Org. Chem.

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“…Mechanistic studies suggest that this reaction involves Mn-catalyzed alkyl radical formation and subsequent azidyl group transfer through Mn III/IV electrocatalysis, which avoids the oxidation to carbocation thus minimizing the side reactions leading to oxygenated products. In addition to these new research articles, we also found a few new review articles that were published during the manuscript review process. − …”

Section: Literature Updates: Additions Made During Manuscript Revisionmentioning

confidence: 99%

New Strategies for the Synthesis of Aliphatic Azides

2021

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Aliphatic azides are a versatile class of compounds found in a variety of biologically active pharmaceuticals. These compounds are also recognized as useful precursors for the synthesis of a range of nitrogen-based scaffolds of therapeutic drugs, biologically active compounds, and functional materials. In light of the growing importance of aliphatic azides in both chemical and biological sciences, a vast array of synthetic strategies for the preparation of structurally diverse aliphatic azides have been developed over the past decades. However, to date, this topic has not been the subject of a dedicated review. This review aims to provide a concise overview of modern synthetic strategies to access aliphatic azides that have emerged since 2010. The discussed azidation reactions include (a) azidation of C–C multiple bonds, (b) azidation of C–H bonds, (c) the direct transformation of vinyl azides into other aliphatic azides, and (d) miscellaneous reactions to access aliphatic azides. We critically discuss the synthetic outcomes and the generality and uniqueness of the different mechanistic rationale of each of the selected reactions. The challenges and potential opportunities of the topic are outlined.

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“…5 However, owing to their inert aromatic C–H bonds the synthesis of aromatic azides is limited in the literature, unlike aliphatic azides. 6–9…”

Section: Introductionmentioning

confidence: 99%

“…5 However, owing to their inert aromatic C-H bonds the synthesis of aromatic azides is limited in the literature, unlike aliphatic azides. [6][7][8][9] Interestingly, it was found that copper can facilitate the synthesis of aromatic azides via C-H functionalization. Aniline, a simple aromatic amine, was converted into its corresponding mono-and di-azides using CuBr (10 mol%) with a yield of 46% and 27%, respectively.…”

Section: Introductionmentioning

confidence: 99%