Palladium-catalyzed cross-coupling of 2-iodobiphenyls with ortho-chloroacetophenones through dual C–H arylation for the construction of tribenzo[a,c,f]cyclooctanones

Zuo, Xiang; Cheng, Cang; Zhang, Yanghui

doi:10.1039/d2qo00647b

Org. Chem. Front.

2022

DOI: 10.1039/d2qo00647b

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Palladium-catalyzed cross-coupling of 2-iodobiphenyls with ortho-chloroacetophenones through dual C–H arylation for the construction of tribenzo[a,c,f]cyclooctanones

Xiang Zuo

Cang Cheng

Yanghui Zhang

Abstract: The palladium-catalyzed cross-coupling reaction of 2-iodobiphenyls with ortho-chloroacetophenones has been developed. The reaction involves C─H activation of 2-iodobiphenyls and yields eight-membered carbocycles by forming two C─C bonds. The protocol provides...

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Cited by 2 publications

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K⁺‐Mediated vs Pd‐Catalyzed Cyclotrimerization of 9,10‐Didehydrotribenzo[8]annulene (TribenzoCOTyne): Stereodivergent Access to (α,α,α)‐ and (α,α,β)‐Fragments of Cubic Graphite

Bello‐García,

Varela,

Saá

2024

Angewandte Chemie

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A remarkable stereodivergent cyclotrimerization of 9,10‐didehydrotribenzo[8]annulene (tribenzoCOTyne) to the corresponding (α,α,α)‐ and (α,α,β)‐benzofused derivatives has been developed by controlling the reaction conditions. While the K+‐mediated cyclotrimerization afforded the (α,α,α) stereoisomer, using Pd as a catalyst resulted in the (α,α,β)‐derivative. Both stereoisomers were evidenced by spectroscopic data and crystal X‐Ray analysis. The (α,α,α) stereoisomer is a fragment of cubic graphite (CG), an elusive 3D carbon allotrope that contains carbon cages, since all of its sixty carbons are part of the structure of CG, and 36 constitute a part of the C48 molecular cage of CG. Experimental and computational mechanistic studies revealed that the potassium ion would play a key role as a template to favor the formation of the (α,α,α) stereoisomer.

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K⁺‐Mediated vs Pd‐Catalyzed Cyclotrimerization of 9,10‐Didehydrotribenzo[8]annulene (TribenzoCOTyne): Stereodivergent Access to (α,α,α)‐ and (α,α,β)‐Fragments of Cubic Graphite

Bello‐García,

Varela,

Saá

2024

Angewandte Chemie

View full text Add to dashboard Cite

show abstract

K⁺‐Mediated vs Pd‐Catalyzed Cyclotrimerization of 9,10‐Didehydrotribenzo[8]annulene (TribenzoCOTyne): Stereodivergent Access to (α,α,α)‐ and (α,α,β)‐Fragments of Cubic Graphite

Bello‐García,

Varela,

Saá

2024

Angew Chem Int Ed

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Palladium-catalyzed cross-coupling of 2-iodobiphenyls with ortho-chloroacetophenones through dual C–H arylation for the construction of tribenzo[a,c,f]cyclooctanones

Abstract: The palladium-catalyzed cross-coupling reaction of 2-iodobiphenyls with ortho-chloroacetophenones has been developed. The reaction involves C─H activation of 2-iodobiphenyls and yields eight-membered carbocycles by forming two C─C bonds. The protocol provides...

Cited by 2 publications

References 59 publications

K⁺‐Mediated vs Pd‐Catalyzed Cyclotrimerization of 9,10‐Didehydrotribenzo[8]annulene (TribenzoCOTyne): Stereodivergent Access to (α,α,α)‐ and (α,α,β)‐Fragments of Cubic Graphite

K⁺‐Mediated vs Pd‐Catalyzed Cyclotrimerization of 9,10‐Didehydrotribenzo[8]annulene (TribenzoCOTyne): Stereodivergent Access to (α,α,α)‐ and (α,α,β)‐Fragments of Cubic Graphite

K⁺‐Mediated vs Pd‐Catalyzed Cyclotrimerization of 9,10‐Didehydrotribenzo[8]annulene (TribenzoCOTyne): Stereodivergent Access to (α,α,α)‐ and (α,α,β)‐Fragments of Cubic Graphite

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Palladium-catalyzed cross-coupling of 2-iodobiphenyls with ortho-chloroacetophenones through dual C–H arylation for the construction of tribenzo[a,c,f]cyclooctanones

Abstract: The palladium-catalyzed cross-coupling reaction of 2-iodobiphenyls with ortho-chloroacetophenones has been developed. The reaction involves C─H activation of 2-iodobiphenyls and yields eight-membered carbocycles by forming two C─C bonds. The protocol provides...

Cited by 2 publications

References 59 publications

K+‐Mediated vs Pd‐Catalyzed Cyclotrimerization of 9,10‐Didehydrotribenzo[8]annulene (TribenzoCOTyne): Stereodivergent Access to (α,α,α)‐ and (α,α,β)‐Fragments of Cubic Graphite

K+‐Mediated vs Pd‐Catalyzed Cyclotrimerization of 9,10‐Didehydrotribenzo[8]annulene (TribenzoCOTyne): Stereodivergent Access to (α,α,α)‐ and (α,α,β)‐Fragments of Cubic Graphite

K+‐Mediated vs Pd‐Catalyzed Cyclotrimerization of 9,10‐Didehydrotribenzo[8]annulene (TribenzoCOTyne): Stereodivergent Access to (α,α,α)‐ and (α,α,β)‐Fragments of Cubic Graphite

Contact Info

Product

Resources

About

K⁺‐Mediated vs Pd‐Catalyzed Cyclotrimerization of 9,10‐Didehydrotribenzo[8]annulene (TribenzoCOTyne): Stereodivergent Access to (α,α,α)‐ and (α,α,β)‐Fragments of Cubic Graphite

K⁺‐Mediated vs Pd‐Catalyzed Cyclotrimerization of 9,10‐Didehydrotribenzo[8]annulene (TribenzoCOTyne): Stereodivergent Access to (α,α,α)‐ and (α,α,β)‐Fragments of Cubic Graphite

K⁺‐Mediated vs Pd‐Catalyzed Cyclotrimerization of 9,10‐Didehydrotribenzo[8]annulene (TribenzoCOTyne): Stereodivergent Access to (α,α,α)‐ and (α,α,β)‐Fragments of Cubic Graphite