Copper‐Catalyzed Diphenylation of P(O)‐OH Bonds with Cyclic Diaryliodonium Salts

Wang, Gang; Xiong, Biquan; Zhou, Congshan; Liu, Yu; Xu, Weifeng; Yang, Changan; Tang, Kewen; Wong, Wai Yeung

doi:10.1002/asia.201901284

Cited by 14 publications

(10 citation statements)

References 58 publications

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“…While our study was progressing,C hen et al,r eported the effect of impurity on the afterglow property of carbazoles. [16] In the purview of this report, we synthesized carbazole in our lab using reported protocols [17] and confirmed the purity by highperformance liquid chromatography (HPLC) using acetonitrile-water mixture (Scheme 1). All the final molecules were also purified similarly and hence,w ew ould like to mention that the concerns related to the effect of impurity on the present work, if any,are not valid.…”

Section: Resultsmentioning

confidence: 72%

Self‐Assembled Helical Arrays for the Stabilization of the Triplet State

Nidhankar

Goudappagouda

Kumari³

et al. 2020

Angewandte Chemie

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Room‐temperature phosphorescence of metal and heavy atom‐free organic molecules has emerged as an area of great potential in recent years. A rational design played a critical role in controlling the molecular ordering to impart efficient intersystem crossing and stabilize the triplet state to achieve room‐temperature ultralong phosphorescence. However, in most cases, the strategies to strengthen phosphorescence efficiency have resulted in a reduced lifetime, and the available nearly degenerate singlet‐triplet energy levels impart a natural competition between delayed fluorescence and phosphorescence, with the former one having the advantage. Herein, an organic helical assembly supports the exhibition of an ultralong phosphorescence lifetime. In contrary to other molecules, 3,6‐phenylmethanone functionalized 9‐hexylcarbazole exhibits a remarkable improvement in phosphorescence lifetime (>4.1 s) and quantum yield (11 %) owing to an efficient molecular packing in the crystal state. A right‐handed helical molecular array act as a trap and exhibits triplet exciton migration to support the exceptionally longer phosphorescence lifetime.

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Section: Resultsmentioning

confidence: 72%

Self‐Assembled Helical Arrays for the Stabilization of the Triplet State

Nidhankar

Goudappagouda

Kumari³

et al. 2020

Angewandte Chemie

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“…Wong et al have developed a facile synthesis of valuable 2′iodo substituted biaryl phosphinic/phosphoric acid esters 102 through copper-catalyzed single arylation of P(O)−OH bonds with cyclic diaryliodoniums 98 (Scheme 30B). 348 Various functional P(O)−OH compounds 101 and a range of substituted cyclic diaryliodoniums 98 are compatible under the optimized reaction conditions. This new synthetic method possesses high potential for further applications, such as the construction of biologically active compounds and chiral phosphine ligands.…”

Section: Construction Of Racemic Biaryl Compoundsmentioning

confidence: 99%

Recent Progress in Cyclic Aryliodonium Chemistry: Syntheses and Applications

et al. 2023

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Hypervalent aryliodoumiums are intensively investigated as arylating agents. They are excellent surrogates to aryl halides, and moreover they exhibit better reactivity, which allows the corresponding arylation reactions to be performed under mild conditions. In the past decades, acyclic aryliodoniums are widely explored as arylation agents. However, the unmet need for acyclic aryliodoniums is the improvement of their notoriously low reaction economy because the coproduced aryl iodides during the arylation are often wasted. Cyclic aryliodoniums have their intrinsic advantage in terms of reaction economy, and they have started to receive considerable attention due to their valuable synthetic applications to initiate cascade reactions, which can enable the construction of complex structures, including polycycles with potential pharmaceutical and functional properties. Here, we are summarizing the recent advances made in the research field of cyclic aryliodoniums, including the nascent design of aryliodonium species and their synthetic applications. First, the general preparation of typical diphenyl iodoniums is described, followed by the construction of heterocyclic iodoniums and monoaryl iodoniums. Then, the initiated arylations coupled with subsequent domino reactions are summarized to construct polycycles. Meanwhile, the advances in cyclic aryliodoniums for building biaryls including axial atropisomers are discussed in a systematic manner. Finally, a very recent advance of cyclic aryliodoniums employed as halogen-bonding organocatalysts is described.

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“…Wang et al 85 combined diaryl phosphinic acid 68 and cyclic diaryliodonium salt 4 in the presence of triethylamine base and tetrahydrofuran (THF) solvent to demonstrate copper-catalyzed synthesis of 2′-iodosubstituted biaryl phosphonic acid esters 69 . The diarylation of P(O)–OH bonds in a mild, atom economical, and ecofriendly manner along with further synthetic and transformation scope of the final product make the strategy valuable and pragmatic.…”

Section: Applications Of Cyclic Diaryliodonium Saltsmentioning

confidence: 99%