One-Step Synthesis of 4H-3,1-Benzoxazin-4-ones from Weinreb Amides and 1,4,2-Dioxazol-5-ones via Cobalt-Catalyzed C–H Bond Activation

Matsunaga, Shigeki; Yoshino, Tatsuhiko; Tanimoto, Iku; Kawai, Kentaro; Sato, Akane

doi:10.3987/com-18-s(f)48

Cited by 14 publications

(1 citation statement)

References 64 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…51 In the case of C-H amidation reactions using dioxazolones as amidation reagents, 52 high temperatures and prolonged reaction times lead to partial cyclization of the products into 4H-3,1-benzoxazin-4ones with the release of N-methoxy-N-methylamine (Scheme 15). 53 The cyclization is reversible, and the yield of the 4H-3,1benzoxazin-4-ones was maximized upon the addition of Ac2O to scavenge N-methoxy-N-methylamine.…”

Section: Other Miscellaneous Reactionsmentioning

confidence: 99%

Cp*CoIII-Catalyzed C–H Functionalization and Asymmetric Reactions Using External Chiral Sources

Yoshino¹,

Matsunaga²

2019

Synlett

Self Cite

View full text Add to dashboard Cite

This account describes Cp*CoIII-catalyzed C–H functionalization reactions developed in our group between 2013 and 2018. Cp*CoIII catalysts not only serve as inexpensive alternatives to Cp*RhIII catalysts but also exhibit unique reactivity and selectivity in several transformations. In the latter part of this review, we introduce catalytic asymmetric C–H functionalization reactions using achiral RhIII or CoIII catalysts with chiral disulfonates or carboxylic acids as external chiral sources.1 Introduction and Overview2 Cp*CoIII-Catalyzed C–H Functionalization Reactions2.1 C–H Addition Reactions to Polar Double Bonds2.2 Cp*Co(CO)I2 and [Cp*CoI2]2 Precursors for the C2-selective C–H Amidation of Indoles2.3 C–H Functionalization of Carbamoyl-Protected Indoles Using Alkynes2.4 C–H Allylation Using Allyl Alcohols2.5 Cyclization Reactions of O-Acyloximes and Alkynes2.6 Other Miscellaneous Reactions3 Enantioselective C–H Functionalization Reactions by Hybrid Catalysis3.1 Cp*RhIII/Chiral Disulfonate Catalysts for the Enantioselective C–H Addition to Enones3.2 Enantioselective C–H Cleavage Using Chiral Carboxylic Acids4 Summary and Perspective

show abstract

Section: Other Miscellaneous Reactionsmentioning

confidence: 99%

Cp*CoIII-Catalyzed C–H Functionalization and Asymmetric Reactions Using External Chiral Sources

Yoshino¹,

Matsunaga²

2019

Synlett

Self Cite

View full text Add to dashboard Cite

show abstract

Cobalt‐Catalyzed CH Activation

Yoshikai¹

2022

Patai's Chemistry of Functional Groups

View full text Add to dashboard Cite

This chapter provides an overview of cobalt‐catalyzed CH activation reactions reported from 2010 to mid‐2020. The reactions are categorized primarily by the nature of the cobalt species (i.e., low or high valent) and secondarily by the type of the reaction partner and/or the transformation. “Low‐valent” cobalt catalysts generally refer to catalysts generated in situ from Co II or Co III precatalysts and reductants or those having well‐defined structures with Co 0 or Co I oxidation state. “High‐valent” cobalt catalysts are typically Co III complexes supported by pentamethylcyclopentadienyl (Cp*) or analogous ligands or cobalt species generated from Co II or Co III precatalysts under oxidative or nonreductive conditions.

show abstract

Cobalt Catalyzed CH Amination and Amidation

Sk¹,

Saha²,

Maji³

2022

Handbook of CH-Functionalization

View full text Add to dashboard Cite

Looking into the increasing requirement for sustainable and environmentally sound chemical processes, employing nonprecious metals, specifically the earth‐abundant ones, is an attractive choice to construct CN bond by CH activation strategy involving the inner‐ or outer‐sphere mechanism. The article described Co(II)–porphyrins and cyclopentadienyl‐ligand‐based catalysts as the new class of effective catalysts for the amination or amidation of C(sp 2 /sp 3 )H bonds, with prominence to access a wide array of nitrogen‐containing compounds including heterocycles, natural products, medicinally significant bioactive molecules, and synthetic intermediates.

show abstract

One-Step Synthesis of 4H-3,1-Benzoxazin-4-ones from Weinreb Amides and 1,4,2-Dioxazol-5-ones via Cobalt-Catalyzed C–H Bond Activation

Cited by 14 publications

References 64 publications

Cp*CoIII-Catalyzed C–H Functionalization and Asymmetric Reactions Using External Chiral Sources

Cp*CoIII-Catalyzed C–H Functionalization and Asymmetric Reactions Using External Chiral Sources

Cobalt‐Catalyzed CH Activation

Cobalt Catalyzed CH Amination and Amidation

Contact Info

Product

Resources

About