A substrate-dependent reaction of 1-aryl-2-alkyl-1,2-diketones with 2-aroyl-1-chlorocyclopropanecarboxylates: selective access to 2′,5′-dicyclopropoxy-1,1′:4′,1′′-teraryls and pentafulvenes

Prakash, Meher; Rani, Poonam; Samanta, Sampak

doi:10.1039/d2ob00971d

Org. Biomol. Chem.

2022

DOI: 10.1039/d2ob00971d

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A substrate-dependent reaction of 1-aryl-2-alkyl-1,2-diketones with 2-aroyl-1-chlorocyclopropanecarboxylates: selective access to 2′,5′-dicyclopropoxy-1,1′:4′,1′′-teraryls and pentafulvenes

Meher Prakash

Poonam Rani

Sampak Samanta

Abstract: An interesting substrate-controlled one-pot approach to highly substituted 2ʹ,5ʹ-dicyclopropoxy-1,1ʹ:4ʹ,1ʺ-teraryls and 6-hydroxypentafulvenes involving various 1,2-diketones and 2-aroyl-1-chlorocyclopropanecarboxylates as 3C Michael acceptors triggered by Cs2CO3 has been developed. We noticed that the...

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Cited by 4 publications

References 95 publications

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α‐Halocarbonyls as a Valuable Functionalized Tertiary Alkyl Source

Nishikata

2024

ChemistryOpen

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This review introduces the synthetic organic chemical value of α‐bromocarbonyl compounds with tertiary carbons. This α‐bromocarbonyl compound with a tertiary carbon has been used primarily only as a radical initiator in atom transfer radical polymerization (ATRP) reactions. However, with the recent development of photo‐radical reactions (around 2010), research on the use of α‐bromocarbonyl compounds as tertiary alkyl radical precursors became popular (around 2012). As more examples were reported, α‐bromocarbonyl compounds were studied not only as radicals but also for their applications in organometallic and ionic reactions. That is, α‐bromocarbonyl compounds act as nucleophiles as well as electrophiles. The carbonyl group of α‐bromocarbonyl compounds is also attractive because it allows the skeleton to be converted after the reaction, and it is being applied to total synthesis. In our survey until 2022, α‐bromocarbonyl compounds can be used to perform a full range of reactions necessary for organic synthesis, including multi‐component reactions, cross‐coupling, substitution, cyclization, rearrangement, stereospecific reactions, asymmetric reactions. α‐Bromocarbonyl compounds have created a new trend in tertiary alkylation, which until then had limited reaction patterns in organic synthesis. This review focuses on how α‐bromocarbonyl compounds can be used in synthetic organic chemistry.

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α‐Halocarbonyls as a Valuable Functionalized Tertiary Alkyl Source

Nishikata

2024

ChemistryOpen

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Organobase-catalyzed Mannich reaction of cyclic N-sulfonyl imines and 1,2-diketones: A sustainable approach to 4-(3-arylquinoxalin-2-ylmethyl)sufamidates

Rani

Prakash

Samanta

2023

Tetrahedron Letters

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Base-promoted cyclization ofortho-hydroxyacetophenones within situgenerated cyclopropenes: diastereoselective access to spirobenzo[b]oxepines and related precursors

Samanta¹,

Prakash

2023

Org. Biomol. Chem.

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A substrate-dependent reaction of 1-aryl-2-alkyl-1,2-diketones with 2-aroyl-1-chlorocyclopropanecarboxylates: selective access to 2′,5′-dicyclopropoxy-1,1′:4′,1′′-teraryls and pentafulvenes

Cited by 4 publications

References 95 publications

α‐Halocarbonyls as a Valuable Functionalized Tertiary Alkyl Source

α‐Halocarbonyls as a Valuable Functionalized Tertiary Alkyl Source

Organobase-catalyzed Mannich reaction of cyclic N-sulfonyl imines and 1,2-diketones: A sustainable approach to 4-(3-arylquinoxalin-2-ylmethyl)sufamidates

Base-promoted cyclization ofortho-hydroxyacetophenones within situgenerated cyclopropenes: diastereoselective access to spirobenzo[b]oxepines and related precursors

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