Evolution of N-Heterocycle-substituted Iodoarenes (NHIAs) to efficient Organocatalysts in Iodine(I/III)-mediated Oxidative Transformations

Boelke, Andreas; Nachtsheim, Boris J.

doi:10.26434/chemrxiv.9963494.v1

Search citation statements

Order By: Relevance

Paper Sections

Select...

Full Paper1

Citation Types

Supporting

Mentioning

Contrasting

Year Published

2019

Publication Types

Select...

Article1

Relationship

Self Cite1

Independent0

Authors

Journals

Cited by 1 publication

(1 citation statement)

References 17 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Compared to the low yield (9%) with iodobenzene (7) as the catalyst, NHIAs 10 e and 10 a gave the rearrangement product 16 in moderate to good yield (34 and 58%). [41]…”

Section: Full Papermentioning

confidence: 99%

Evolution of N‐Heterocycle‐Substituted Iodoarenes (NHIAs) to Efficient Organocatalysts in Iodine(I/III)‐Mediated Oxidative Transformations

Boelke

Nachtsheim

2019

Adv Synth Catal

Self Cite

View full text Add to dashboard Cite

The reactivity of ortho‐functionalized N‐heterocycle‐substituted iodoarenes (NHIAs) as organocatalysts in iodine(I/III)‐mediated oxidations was systematically investigated in the α‐tosyloxylation of ketones as the model reaction. During a systematic catalyst evolution, it was found that NH‐triazoles and benzoxazoles have the most significant positive influence on the reactivity of the central iodine atom. A further catalyst improvement which focused on the substitution pattern of the arene revealed a remarkable ortho‐effect. By introduction of an o‐OMe group we were able to generate a novel NHIA with a so far unseen catalytic efficiency. This new catalyst is not only easy to synthesize but also enabled the α‐tosyloxylation of carbonyl compounds at the lowest reported catalyst loading of only 1 mol%. Finally, the performance of this iodine(I) catalyst was successfully demonstrated in intramolecular oxidative couplings of biphenyls and oxidative rearrangements.

show abstract

“…Compared to the low yield (9%) with iodobenzene (7) as the catalyst, NHIAs 10 e and 10 a gave the rearrangement product 16 in moderate to good yield (34 and 58%). [41]…”

Section: Full Papermentioning

confidence: 99%