Correction: nBu<sub>4</sub>NI-Mediated oxidation of methyl ketones to α-ketoamides: using ammonium, primary and secondary amine-salt as an amine moiety

Wang, Dan; Lu-han, Jia; Zhang, Danting; Zhang, Yue; Cheng, Yujia; Lin, Chin‐Wen; Wang, Bo

doi:10.1039/c7ob90088k

Cited by 7 publications

(5 citation statements)

References 2 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Lin and co‐workers [54] employed thiols as precursors of N ‐thiopyrrolidine 41.1 in the presence of NBS. The thirranium formation and ring‐opening addition strategy worked well for the thiolation‐amidation 41.2 of alkenes.…”

Section: Thiolationmentioning

confidence: 99%

Recent Developments in Selenylation and Thiolation of Alkenes via Three‐component Reactions

Huang

Wang

et al. 2023

Adv Synth Catal

View full text Add to dashboard Cite

Alkenes are valuable feedstocks in organic synthesis. Selenium or sulfur-containing coumpounds with a neighboring functional group can be easily prepared by direct difunctionalization of alkenes via three-component reactions. It will reduce the number of steps and waste generation, and form complicated molecules from simple starting materials. Herein, recent developments (2013-2022) have been summarized via two categories: (1) selenylation via seleniranium intermediates or Se-centered radicals;(2) thiolation with more diverse mechanisms and products Reactions with electron-rich arenes, alcohols, water, acids, NaN 3 , amines, KSCN, and sulfamides, TMSNCS, TMSN 3 , Et 3 N • 3HF, SOCl 2 , HCl, NFSI, t BuONO, pyridinium salts, t BuOOH, ArN 2 BF 4 , CO 2 , CO, O 2 , CF 3 SO 2 Cl, R 2 P(O)À H, (RO) 2 P(O)SH, (RO) 2 P(O)OH et al will be discussed.We hope this review will do help for future research in this area.1. Thiolation 3.1. Synthesis of Sulfides 3.2. Synthesis of Sulfoxides 3.3. Synthesis of Sulfones 4.Conclusions and Outlook

show abstract

Section: Thiolationmentioning

confidence: 99%

Recent Developments in Selenylation and Thiolation of Alkenes via Three‐component Reactions

Huang

Wang

et al. 2023

Adv Synth Catal

View full text Add to dashboard Cite

show abstract

“…Song and Chen research groups revealed that PIDA oxidation in conjunction with an AgSbF 6 catalyst allowed for the selective C−H selenylation of indole scaffolds ( 231 ) at the C5 position, resulting in the creation of a variety of otherwise challenging to prepare 5‐selenylated indole derivatives ( 232 ) (Scheme 81). [161] The tethered C3 pivaloyl group on indole scaffolds had a function in both blocking the active C3 position and adjusting the electrical affinity of the arenes, according to mechanistic investigations, which showed that current transformation follows a radical process.…”

Section: Applications Of Phenyliodine(iii)diacetatementioning

confidence: 99%

Applications of Phenyliodine(III)diacetate in C−H Functionalization and Hetero‐Hetero Bond Formations: A Septennial Update

et al. 2023

View full text Add to dashboard Cite

One of the most widely utilized hypervalent iodines used as an oxidizing agent in organic chemistry is (diacetoxyiodo)benzene (PhI(OAc)2), also known as (DAIB), phenyliodine(III) diacetate (PIDA). In this review, authors have comprehensively and systematically presented the various applications of PIDA in organic synthesis involving C−C, C‐hetero, hetero‐hetero and multiple bond forms from the summer of 2015 to the present. The role of PIDA was also emphasized for the success of particular organic transformation. Recent literature has produced a substantial number of publications (∼100), and this septennial review examines all of the most recent breakthroughs in the field of study.

show abstract

“…α ‐Ketoamides have attracted considerable interest due to their potential ability as versatile synthetic motifs in numerous natural products, biological drug candidates and functional group transformations . Various approaches have been proposed in the synthesis of a diverse array of α ‐ketoamides from different ketones and amines . Recently, the iodine‐driven reaction have emerged as a powerful strategy because of the particularly reactive halogen bond‐based systems.…”

Section: Introductionmentioning

confidence: 99%

“…In classical amidations with the addition of iodine (I 2 ), the amine is recognized as the reactant, and I 2 is almost presumed to play the catalytic role . Our previous studies reported the preparation of diverse α ‐ketoamides under clean and mild conditions from varying substrates including aryl methyl ketones . Currently, there are two issues involved with the direct amidation.…”

Section: Introductionmentioning

confidence: 99%

Unveiling the reaction process of the amine in direct amidation of aromatic ketones in H₂O

et al. 2020

ChemistryOpen

Self Cite

View full text Add to dashboard Cite

In the classical amidation between aromatic ketones and amines, 2.0 equivalents of amines are necessarily required to gain satisfying yields. The specific role of the amine in the direct amidation already puzzled us for a long time. In this work, we disclosed that the amine acts as both reactant and catalyst. Specifically, the determination of reaction intermediates revealed the full mechanism, based on which, the introduction of one equivalent base in the amidation is showcased here that a high yield (∼95 %) can be afforded using only 1.1 equiv. of amine.

show abstract

Correction: nBu₄NI-Mediated oxidation of methyl ketones to α-ketoamides: using ammonium, primary and secondary amine-salt as an amine moiety

Abstract: Correction for 'nBuNI-Mediated oxidation of methyl ketones to α-ketoamides: using ammonium, primary and secondary amine-salt as an amine moiety' by Dan Wang et al., Org. Biomol. Chem., 2017, 15, 3427-3434.

Cited by 7 publications

References 2 publications

Recent Developments in Selenylation and Thiolation of Alkenes via Three‐component Reactions

Recent Developments in Selenylation and Thiolation of Alkenes via Three‐component Reactions

Applications of Phenyliodine(III)diacetate in C−H Functionalization and Hetero‐Hetero Bond Formations: A Septennial Update

Unveiling the reaction process of the amine in direct amidation of aromatic ketones in H₂O

Contact Info

Product

Resources

About

Correction: nBu4NI-Mediated oxidation of methyl ketones to α-ketoamides: using ammonium, primary and secondary amine-salt as an amine moiety

Abstract: Correction for 'nBuNI-Mediated oxidation of methyl ketones to α-ketoamides: using ammonium, primary and secondary amine-salt as an amine moiety' by Dan Wang et al., Org. Biomol. Chem., 2017, 15, 3427-3434.

Cited by 7 publications

References 2 publications

Recent Developments in Selenylation and Thiolation of Alkenes via Three‐component Reactions

Recent Developments in Selenylation and Thiolation of Alkenes via Three‐component Reactions

Applications of Phenyliodine(III)diacetate in C−H Functionalization and Hetero‐Hetero Bond Formations: A Septennial Update

Unveiling the reaction process of the amine in direct amidation of aromatic ketones in H2O

Contact Info

Product

Resources

About

Correction: nBu₄NI-Mediated oxidation of methyl ketones to α-ketoamides: using ammonium, primary and secondary amine-salt as an amine moiety

Unveiling the reaction process of the amine in direct amidation of aromatic ketones in H₂O