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Heterocyclic amines, where the N atom is a part of an alicyclic system, are similar in basicity to alkylamines. Interestingly, the heterocyclic amine having a nitrogen atom as part of an aromatic ring has much less basicity than its corresponding alicyclic counterpart. For this reason, as presented in Figure 1, piperidine (pKb = 2.8) is significantly more basic than pyridine (pKb = 8.8).
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All ortho–para directors, excluding halogens, are activating groups. These groups donate electrons to the ring, making the ring carbons electron-rich. Consequently, the reactivity of the aromatic ring towards electrophilic substitution increases. For instance, the nitration of anisole is about 10,000 times faster than the nitration of benzene. The electron-donating effect of the methoxy group in anisole activates the ortho and para positions on the ring and stabilizes the corresponding...
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Monoaurated vs. diaurated intermediates: causality or independence?

Mariarosa Anania1, Lucie Jašíková1, Jan Zelenka2

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Gold catalysis research clarifies reaction intermediates. This study reveals that mono-gold ketone intermediates, not dual-gold species, drive the water addition to alkynes reaction mechanism.

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Area of Science:

  • Organometallic Chemistry
  • Catalysis
  • Reaction Mechanisms

Background:

  • The role of diaurated intermediates in gold-catalyzed reactions remains debated, with conflicting views on their involvement as active species or inactive byproducts.
  • Previous studies have proposed dual-gold cooperation in some reactions, while others suggested diaurated complexes merely drain active mono-gold species.

Purpose of the Study:

  • To investigate the nature and role of intermediates in gold-catalyzed water addition to alkynes.
  • To elucidate the reaction mechanism and determine whether mono- or diaurated species are the active intermediates.

Main Methods:

  • Electrospray ionization mass spectrometry (ESI-MS) to detect mono- and diaurated complexes.
  • Infrared photodissociation spectroscopy to determine the structures of trapped intermediates.
  • Delayed reactant labeling experiments to measure intermediate half-lives and kinetic isotope effects (KIEs).
  • Kinetic analysis to determine reaction order with respect to the gold catalyst concentration.

Main Results:

  • ESI-MS detected both mono- and diaurated complexes, identified as protonated or oxygen-aurated α-gold ketone intermediates.
  • Kinetic studies revealed similar or identical kinetics for mono- and diaurated species detected by ESI-MS.
  • Kinetic isotope effects for hydrogen introduction (KIE ~ 4-6) and protodeauration (KIE ~ 2) were measured.
  • The overall reaction rate was found to be first-order dependent on the gold catalyst concentration.

Conclusions:

  • The experimental evidence strongly supports a reaction mechanism proceeding exclusively through mono-gold neutral α-gold ketone intermediates.
  • Diaurated species detected in situ do not represent a distinct mechanistic pathway but likely reflect species with similar kinetic behavior to the active mono-gold intermediates.
  • This study resolves the long-standing debate regarding the role of diaurated intermediates in this class of gold-catalyzed reactions.