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2 article(s) from Montgomery, Carlee A

Direct trifluoroethylation of carbonyl sulfoxonium ylides using hypervalent iodine compounds

Radell Echemendía,
Carlee A. Montgomery,
Fabio Cuzzucoli,
Antonio C. B. Burtoloso and
Graham K. Murphy

Beilstein J. Org. Chem. 2024, 20, 3182–3190, doi:10.3762/bjoc.20.263

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Figure 1: Representative examples of fluorine containing, biologically active compounds.

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Scheme 1: Strategies for the synthesis of α-alkyl sulfoxonium ylides.

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Scheme 2: Exploring substrate scope in the direct α-fluoroalkylation of sulfoxonium ylides.

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Scheme 3: Synthetic applications of fluoroalkylated sulfoxonium ylides.

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Figure 2: Possible mechanisms for the reaction of 1a and 2a leading to 3a (via B), proceeding via either halo...

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Figure 3: Electrostatic potential of 2a’ from 0.075 e to 0.21 e, showing two sigma holes of potentials 0.20 a...

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Figure 4: The optimized reaction coordinate diagrams for the halogen bond-mediated mechanism (path 1, left) a...

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Full Research Paper

Published 04 Dec 2024

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Exploring the role of halogen bonding in iodonium ylides: insights into unexpected reactivity and reaction control

Carlee A. Montgomery and
Graham K. Murphy

Beilstein J. Org. Chem. 2023, 19, 1171–1190, doi:10.3762/bjoc.19.86

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Figure 1: Generic representation of halogen bonding.

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Figure 2: Quantitative evaluation of σ-holes in monovalent iodine-containing compounds; and, qualitative mole...

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Figure 3: Quantitative evaluation of σ-holes in hypervalent iodine-containing molecules; and, qualitative MEP...

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Figure 4: Quantitative evaluation of σ-holes in iodonium ylides; and, qualitative MEP map of I-12 from −0.083...

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Scheme 1: Outline of possible reaction pathways between iodonium ylides and Lewis basic nucleophiles (top); a...

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Scheme 2: Metal-free cyclopropanations of iodonium ylides, either as intermolecular (a) or intramolecular pro...

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Figure 5: Zwitterionic mechanism for intramolecular cyclopropanation of iodonium ylides (left); and, stepwise...

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Scheme 3: Metal-free intramolecular cyclopropanation of iodonium ylides.

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Figure 6: Concerted cycloaddition pathway for the metal-free, intramolecular cyclopropanation of iodonium yli...

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Scheme 4: Reaction of ylide 6 with diphenylketene to form lactone 24 and 25.

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Figure 7: Nucleophilic (top) and electrophilic (bottom) addition pathways proposed by Koser and Hadjiarapoglo...

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Scheme 5: Indoline synthesis from acyclic iodonium ylide 31 and tertiary amines.

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Scheme 6: N-Heterocycle synthesis from acyclic iodonium ylide 31 and secondary amines.

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Figure 8: Proposed mechanism for the formation of 33a from iodonium ylides and amines, involving an initial h...

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Scheme 7: Indoline synthesis from acyclic iodonium ylides 39 and tertiary amines under blue light photocataly...

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Scheme 8: Metal-free cycloproponation of iodonium ylides under blue LED irradiation. ^aUsing trans-β-methylsty...

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Figure 9: Proposed mechanism of the cyclopropanation between iodonium ylides and alkenes under blue LED irrad...

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Scheme 9: Formal C–H alkylation of iodonium ylides by nucleophilic heterocycles under blue LED irradiation.

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Figure 10: Proposed mechanism of the formal C–H insertion of pyrrole under blue LED irradiation.

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Scheme 10: X–H insertions between iodonium ylides and carboxylic acids, phenols and thiophenols.

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Figure 11: Mechanistic proposal for the X–H insertion reactions of iodonium ylides.

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Scheme 11: Radiofluorination of biphenyl using iodonium ylides 54a–e derived from various β-dicarbonyl auxilia...

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Scheme 12: Radiofluorination of arenes using spirocycle-derived iodonium ylides 56.

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Scheme 13: Radiofluorination of arenes using SPIAd-derived iodonium ylides 58.

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Figure 12: Calculated reaction coordinate for the radiofluorination of iodonium ylide 60.

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Scheme 14: Radiofluorination of iodonium ylides possessing various ortho- and para-substituents on the iodoare...

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Figure 13: Difference in Gibbs activation energy for ortho- or para-anisyl derived iodonium ylides 63a and 63b....

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Figure 14: Proposed equilibration of intermediates to transit between 64a (the initial adduct formed between 6...

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Scheme 15: Comparison of 31 and ortho-methoxy iodonium ylide 39 in rhodium-catalyzed cyclopropanation and cycl...

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Figure 15: X-ray crystal structure of dimeric 39 [6], (CCDC# 893474) [143,144].

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Scheme 16: Enaminone synthesis using diazonium and iodonium ylides.

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Figure 16: Transition state calculations for enaminone synthesis from iodonium ylides and thioamides.

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Scheme 17: The reaction between ylides 73a–f and N-methylpyrrole under 365 nm UV irradiation.

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Figure 17: Crystal structures of 76c (top) and 76e (bottom) [101], (CCDC# 2104180 & 2104181) [143,144].

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Published 07 Aug 2023

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