Transition-Metal-Free Benzannulation of Tricarbonyl Derivatives with Arynes: Access to 1,3-Dinaphthol Precursors for the Synthesis of Rhodamine Dye Analogues

Ghotekar, Ganesh S.; Shaikh, Aslam C.; Muthukrishnan, M.

doi:10.1021/acs.joc.8b02560

Cited by 16 publications

(10 citation statements)

References 51 publications

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“…More importantly, this research is in line with the recent call to adopt overarching theoretical frameworks to explain associated psychological phenomena [60]. Both, the processing of social exclusion and the processing of loss of control, can be explained in terms of an expectancy violation process.…”

Section: Discussionsupporting

confidence: 74%

Loss of control as a violation of expectations: Testing the predictions of a common inconsistency compensation approach in an inclusionary cyberball game

2019

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Personal control relies on the expectation that events are contingent upon one’s own behavior. A common ‘inconsistency compensation approach’ posits that a violation of expectancies in social interaction triggers aversive arousal and compensatory effort. Following this approach, we tested the hypothesis that interventions affecting participants' decisions violate the expected personal control. In a modified version of the established cyberball paradigm, participants were not excluded, but consistently included. However, their decisions regarding the recipient of a ball throw in the virtual game were occasionally overruled (expectancy violation). We hypothesized that this intervention will trigger a P3 response in event-related brain potentials (ERP). Since this component is related to subjective expectancies, its amplitude was assumed to depend on the frequency of interventions (independent factor: loss of control). Further, we manipulated the vertical position of the participants’ avatar on the computer screen (independent factor: verticality). Building on research showing that verticality is related to the self-assigned power and influences the expected level of control, we hypothesized that the ERP effects of intervention should be more pronounced for participants with avatars in superior position. As predicted, both experimental factors interactively affected the expression of the ERP response: In case of low intervention frequency, P3 amplitudes were significantly pronounced if the participants’ avatar was positioned above as compared to below co-players (high > low self-assigned power). The effect of verticality could be traced back to a lack of adaptation of P3 amplitudes to recurring aversive events. By demonstrating that loss of control triggers ERP effects corresponding to those triggered by social exclusion, this study provides further evidence for a common cognitive mechanism in reactions to aversive events based on an inconsistency in expectancy states.

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Section: Discussionsupporting

confidence: 74%

Loss of control as a violation of expectations: Testing the predictions of a common inconsistency compensation approach in an inclusionary cyberball game

2019

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“…Mechanistically, after nucleophilic addition to form intermediate 9-215 , the generated aryl anion preferentially attacks the more electrophilic ketone carbonyl group, hence, exclusively affording intermediate 9-216 . In 2019, Muthukrishnan et al accomplished a benzannulation reaction of 1,3-oxopentanedioates 9-217 with o -silylaryl triflates, giving rise to highly functionalized naphthalene derivatives 9-218 in moderate to high yields (Scheme b) . Furthermore, they converted the naphthalene derivatives into a series of rhodamine dye analogues.…”

Section: Cascade or Tandem Reactionsmentioning

confidence: 99%

o-Silylaryl Triflates: A Journey of Kobayashi Aryne Precursors

2021

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Arynes are among the most active organic intermediates and have found numerous applications in expeditious preparation of substituted arenes. In the past 20 years, chemists have witnessed a resurgence in aryne chemistry, which is mainly attributed by the extensive utilization of Kobayashi's method, a fluoride-induced removal of the TMS group with concomitant departure of its ortho OTf group on o-silylaryl triflates. Nowadays, o-silylaryl triflates are the most frequently employed aryne precursors. This review provides an overview of the history of Kobayashi's method, its methodological achievements, and its applications in the synthesis of natural products, bioactive molecules, and polycyclic aromatic hydrocarbons.

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“…)-mediated benzannulation [7] and so on. Alternatively, transition metal-free strategies, including Lewis acid-, [8] Brønsted acid-, [9] water-, [10] benzyne-, [11] and base- [12] catalyzed/mediated benzannulation reactions have emerged as powerful methods for the construction of aromatics. Moreover, the synthesis of cyclic compounds through photocatalytic reaction is also regarded as a green and efficient strategy in recent years.…”

Section: Introductionmentioning

confidence: 99%

Recent Advances in Organocatalyst‐Mediated Benzannulation Reactions

2020

Adv Synth Catal

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Aromatic compounds are omnipresent in organic chemistry, which are the broadest skeletons of bioactive molecules, medicines, and materials. Due to their importance, conventional methods to assemble aromatic rings have attracted considerable attention. The direct formation of benzene cores from readily available acyclic precursors offers a highly versatile and superior approach to prepare both small organic molecules and sophisticated natural products. Recently, organocatalyst-mediated annulation reaction, including phosphine-, tertiary amine-, secondary amine-, primary amine-, and NHC-mediated benzannulation reactions, is considered as an efficient method to access multi-substituted arenes. In this review, we will emphasize the selected examples of organocatalyst-mediated benzannulation reactions of available acyclic precursors for the construction of diverse aromatics.

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Transition-Metal-Free Benzannulation of Tricarbonyl Derivatives with Arynes: Access to 1,3-Dinaphthol Precursors for the Synthesis of Rhodamine Dye Analogues

Cited by 16 publications

References 51 publications

Loss of control as a violation of expectations: Testing the predictions of a common inconsistency compensation approach in an inclusionary cyberball game

Loss of control as a violation of expectations: Testing the predictions of a common inconsistency compensation approach in an inclusionary cyberball game

o-Silylaryl Triflates: A Journey of Kobayashi Aryne Precursors

Recent Advances in Organocatalyst‐Mediated Benzannulation Reactions

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