Cp*Co<sup>III</sup>–Catalyzed<i>syn</i>-Selective C–H Hydroarylation of Alkynes Using Benzamides: An Approach Toward Highly Conjugated Organic Frameworks

Bera, Sourav Sekhar; Debbarma, Suvankar; Ghosh, Avick Kumar; Chand, Santanu; Maji, Modhu Sudan

doi:10.1021/acs.joc.6b02516

Cited by 49 publications

(23 citation statements)

References 80 publications

(22 reference statements)

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“…Subsequently, Co(III)‐catalyzed alkenylation of arene moiety with internal alkyne was reported by Maji and co‐workers (Scheme ) . The method also showed excellent syn ‐hydroarylation, good functional group compatibility and a library of mono and dialkenylated benzamide derivatives were synthesized.…”

Section: Construction Of C−c Bondmentioning

confidence: 99%

Developments in Cp*Co^III‐Catalyzed C−H Bond Functionalizations

Ghorai¹,

Anbarasan²

2019

Asian J Org Chem

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Transition-metal-catalyzed CÀ H bond functionalization has emerged as a powerful tool in contemporary organic synthesis. In this aspect, precious metal-based high-valent catalysts have been extensively studied. In the past decade, earth-abundant high-valent Cp*Co(III)-catalysts have emerged as a promising alternative to the expensive transition metals, providing unique selectivity and reactivity. In this Minireview, we summarized important progresses in the area of Cp*Co (III)-catalyzed CÀ H bond functionalization until 2017.[a] Mr. . Alkylation of CÀ H bonds with activated alkene. Scheme 3. Alkylation of CÀ H bonds with activated alkene. Scheme 4. Alkylation of CÀ H bonds with maleimides.Scheme 5. Alkylation of CÀ H bonds of (hetero)arene with maleimide. Scheme 6. Alkylation of CÀ H bonds with unactivated alkenes. Scheme 7. Allylation of CÀ H bonds with allyl carbonates. . Allylation of CÀ H bonds with allyl acetate. Scheme 9. Allylation of CÀ H bonds of arenes with allyl carbonates. Scheme 10. Allylation of CÀ H bonds with allyl alcohol. Scheme 11. Cobalt catalyzed allylation using allyl alcohol. Scheme 12. Cobalt catalyzed allylation with activated allylating reagent. . Cobalt catalyzed selective addition of C2À H bond to C=N bond. Scheme 18. Cobalt catalyzed selective addition of CÀ H bond to isocyanate. Scheme 19. Cobalt(III)-catalyzed aryl and alkenyl CÀ H aminocarbonylation. Scheme 20. Cobalt catalyzed hydroarylation to ketenimines. Scheme 21. Cobalt catalyzed synthesis of pyrroloindolones. Scheme 22. Cobalt catalyzed alkenylation through hydroarylation to alkyne. Co(III)-catalyzed alkenylation. Scheme 24. Cobalt catalyzed alkenylation of heterocyclic moiety. Scheme 25. Cp*Co III -Catalyzed branch-selective hydroarylation of alkynes. Scheme 26. Cobalt catalyzed C(sp 3 )À H alkenylation. . Cobalt(III)-catalyzed amidation with dioxazolone. Scheme 40. Mechanism of cobalt catalyzed amidation with dioxazolone. Scheme 41. Cobalt(III)-catalyzed CÀ H bond amidation using dioxazolone.

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Section: Construction Of C−c Bondmentioning

confidence: 99%

Developments in Cp*Co^III‐Catalyzed C−H Bond Functionalizations

Ghorai¹,

Anbarasan²

2019

Asian J Org Chem

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“…Also, several of the heterocycle syntheses shown in the previous Schemesh ave an alkenylation step using an alkyne in their reaction sequence;h owever in those examples the intermediate olefine products were not isolated.N ot surprisingly, this has been realized on an umber of examples, for example, pyrroles [147] and benzamides. [148] The group of Sundararaju used 8methylquinoline 206 as starting material, which is the first example of aC (sp 3 )ÀHa lkenylation using this set of reaction conditions (Scheme 40). [149] In most examples R 1 and R 2 werei dentical with n-butyl, which led to high yields between 62-86 %o f 207 (14 examples in total).…”

Section: Scheme27 Aminoquinoline As Powerfuldgi Nc (Sp 3 )àHa Ctivatmentioning

confidence: 99%

Direct Functionalization of C−H Bonds by Iron, Nickel, and Cobalt Catalysis

Pototschnig

Maulide

Schnürch

2017

Chemistry A European J

182

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Non-precious-metal-catalyzed reactions are of increasing importance in chemistry due to the outstanding ecological and economic properties of these metals. In the subfield of metal-catalyzed direct C-H functionalization reactions, recent years have shown an increasing number of publications dedicated to this topic. Nickel, cobalt, and last but not least iron, have started to enter a field which was long dominated by precious metals such as palladium, rhodium, ruthenium, and iridium. The present review article summarizes the development of iron-, nickel-, and cobalt-catalyzed C-H functionalization reactions until the end of 2016, and discusses the scope and limitations of these transformations.

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“…Later, Maji’s group reported an N - tert -butyl amide-directed mono- and di-alkenylation reactions using a cobalt catalyst (Scheme 14) [58]. The reaction was also applied for the preparation of π-conjugated alkenes by four-fold C–H activation, which was found to be fluorescence active.…”

Section: Reviewmentioning

confidence: 99%

Hydroarylations by cobalt-catalyzed C–H activation

Santhoshkumar¹,

Cheng²

2018

Beilstein J. Org. Chem.

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As an earth-abundant first-row transition metal, cobalt catalysts offer a broad range of economical methods for organic transformations via C–H activation. One of the transformations is the addition of C–H to C–X multiple bonds to afford alkylation, alkenation, amidation, and cyclization products using low- or high-valent cobalt catalysts. This hydroarylation is an efficient approach to build new C–C bonds in a 100% atom-economical manner. In this review, the recent developments of Co-catalyzed hydroarylation reactions and their mechanistic studies are summarized.

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Cp*Co^III–Catalyzedsyn-Selective C–H Hydroarylation of Alkynes Using Benzamides: An Approach Toward Highly Conjugated Organic Frameworks

Cited by 49 publications

References 80 publications

Developments in Cp*Co^III‐Catalyzed C−H Bond Functionalizations

Developments in Cp*Co^III‐Catalyzed C−H Bond Functionalizations

Direct Functionalization of C−H Bonds by Iron, Nickel, and Cobalt Catalysis

Hydroarylations by cobalt-catalyzed C–H activation

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Cp*CoIII–Catalyzedsyn-Selective C–H Hydroarylation of Alkynes Using Benzamides: An Approach Toward Highly Conjugated Organic Frameworks

Cited by 49 publications

References 80 publications

Developments in Cp*CoIII‐Catalyzed C−H Bond Functionalizations

Developments in Cp*CoIII‐Catalyzed C−H Bond Functionalizations

Direct Functionalization of C−H Bonds by Iron, Nickel, and Cobalt Catalysis

Hydroarylations by cobalt-catalyzed C–H activation

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Product

Resources

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Cp*Co^III–Catalyzedsyn-Selective C–H Hydroarylation of Alkynes Using Benzamides: An Approach Toward Highly Conjugated Organic Frameworks

Developments in Cp*Co^III‐Catalyzed C−H Bond Functionalizations

Developments in Cp*Co^III‐Catalyzed C−H Bond Functionalizations