Transition metal catalyzed carboannulation of diazabicyclic alkenes with ambiphilic bifunctional reagents: a facile route towards functionalized indanones and indanols

Joseph, Nayana; John, Jubi; Rajan, Rani; Thulasi, Sreeja; Mohan, Anupa; Suresh, Eringathodi; Radhakrishnan, K. V.

doi:10.1016/j.tet.2011.04.087

Cited by 16 publications

(9 citation statements)

References 73 publications

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“…In the same report, we also described a palladium catalyzed carbonylative cyclization of diazabicyclic olefins with 2-formylphenylboronic acid. [40] We observed the exclusive formation of 3,4-disubstituted cyclopentenes under palladium catalysis at room temperature. Annulation product, indanol was obtained in 49 % yield when the solvent was changed from MeOH to CH 3 CN.…”

Section: Eurjocmentioning

confidence: 80%

“…The reaction of 2-iodobenzonitrile 110 with diazabicyclic olefin in the presence of palladium catalysts afforded annulated indanone 111b (Scheme 43). [40] Various reaction parameters like palladium catalysts, solvents and bases were screened to obtain the best conditions for the transformation. Finally, use of 1:1 mixture of olefin and o-iodobenzonitrile in the presence of 10 mol-% Pd 2 (dba) 3 •CHCl 3 , 10 mol-% PPh 3 and 2 equiv.…”

Section: Eurjocmentioning

confidence: 99%

“…Next we examined the reactivity of 2-cyanophenyl-and 2-formylphenyl-boronic acids with azabicyclic alkenes under rhodium catalyzed conditions. [40] Presence of both nucleophilic and electrophilic centres makes them attractive reaction partners for annulation reactions. While nucleophilic carbon-boron linkage can be transmetalated to an organorhodium(I) species, the electrophilic cyano/formyl group can act as an acceptor for an organorhodium(I) species.…”

Section: Eurjocmentioning

confidence: 99%

“…Independent reports from Micouins' and our laboratory have depicted the reactivity of alcohols (or Phenols) and aldehydes with bicyclic olefins. [ 18,40 ] This made us think about the possibility of using salicylaldehyde in which both hydroxyl and aldehyde functionalities are present. Thus, when salicylaldehyde was treated with diazabicyclic olefin in the presence of Rh/Cu catalyst system, cyclopentannulated chromanone was formed in 46 % yield.…”

Section: Desymmetrization Of Diazanorbornenesmentioning

confidence: 99%

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Diazanorbornene: A Valuable Synthon towards Carbocycles and Heterocycles

Preethanuj

Jijy²,

Prakash

et al. 2020

Eur J Org Chem

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Desymmetrization of meso compounds is well recognized as a powerful method for delivering biologically relevant molecular skeletons in a few synthetic steps. Heterobicyclic olefins are a class of meso compounds which exhibit exceptional reactivity due to their high ring strain originating from the unfavorable bond angles and eclipsing interactions. Extensive research was carried out towards the synthetic transformations of oxa-, aza-, and diazanorbornenes/norbornadienes for the synthesis of a wide variety of carbocycles and heterocycles in a

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Section: Eurjocmentioning

confidence: 80%

Section: Eurjocmentioning

confidence: 99%

Section: Eurjocmentioning

confidence: 99%

Section: Desymmetrization Of Diazanorbornenesmentioning

confidence: 99%

See 2 more Smart Citations

Diazanorbornene: A Valuable Synthon towards Carbocycles and Heterocycles

Preethanuj

Jijy²,

Prakash

et al. 2020

Eur J Org Chem

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“…Kaufmann and co‐workers explored the palladium catalyzed hydroarylation of diazabicyclic olefins . Our group has demonstrated the utility of mono and bi‐functional aryl iodides with diazabicyclic olefins toward the construction of 3,4‐disubstituted cyclopentenes, indanones and indoline/benzofuran fused cyclopentenes…”

Section: Introductionmentioning

confidence: 99%

Palladium‐Catalyzed Cross‐Coupling of Aryl Iodides with Heterobicyclic Olefins: Access to Hydroarylated and Heteroannulated Motifs

et al. 2017

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Transition metal catalyzed synthetic transformations of bicyclic olefins have acquired considerable attention towards the construction of biologically relevant carbocycles and heterocycles. In this regard, urea derived bicyclic olefins grabbed our attention due to its tremendous biological significance and synthetic potential. Herein, we report a palladium catalyzed reductive Heck reaction of urea‐derived bicyclic olefins toward the synthesis of hydroarylated and heteroannulated motifs using aryl iodides. The reaction of aryl iodides in the presence of a hydrogen donor such as formic acid furnished the hydroarylated products in moderate to excellent yields. Heteroannulated products such as dihydrobenzofuran derivatives were obtained in moderate to good yields with 2‐iodophenols in the absence of a hydrogen donor. We were also successful in extending this strategy to 2‐iodobenzylbromide and 2‐iodobenzonitrile towards the synthesis of ring fused indane and indanone derivatives. To our dismay, the reactions with 2‐iodoaniline to provide the expected indoline derivatives remained futile. The presence of biologically significant urea moieties coupled with naturally as well as pharmaceutically prevalent carbo/heterocyclic derivatives in the products authenticate the relevance of the current synthetic strategy.

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Boron Reagents and Catalysts for the Functionalization of Strained Heterocycles

Pineschi

2021

Adv Synth Catal

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The particular nature of boron compounds allows an ample modularity of their properties ranging from Lewis acids, C‐nucleophiles, B‐nucleophiles, or even conjunctive reagents for new synthetic manipulations. Moreover, the increasing demand for functionalized boron derivatives for pharmaceutical or material science applications requires the development of new synthetic methods for boron introduction in organic compounds. This review summarizes the possible combinations of boron derivatives with a variety of strained heterocycles reported in the most recent literature.

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Transition metal catalyzed carboannulation of diazabicyclic alkenes with ambiphilic bifunctional reagents: a facile route towards functionalized indanones and indanols

Cited by 16 publications

References 73 publications

Diazanorbornene: A Valuable Synthon towards Carbocycles and Heterocycles

Diazanorbornene: A Valuable Synthon towards Carbocycles and Heterocycles

Palladium‐Catalyzed Cross‐Coupling of Aryl Iodides with Heterobicyclic Olefins: Access to Hydroarylated and Heteroannulated Motifs

Boron Reagents and Catalysts for the Functionalization of Strained Heterocycles

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