The Missing Chalcogen Bonding Donor: Strongly Polarized Oxygen of Water

Zhang, Qinpeng; Luo, Ke; Zhou, Wei; Li, Aimin; He, Qing

doi:10.1021/jacs.3c13604

Cited by 6 publications

(1 citation statement)

References 42 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The significant role of chalcogen bonding in catalysis was recently reported . Recently, He and co-workers have shown that a metal bound water molecule acts as an electron acceptor in chalcogen bonds . The influence of the metal and donor ability of diyne substituents are well-known to influence the regiochemical outcome of C–H functionalization/diyne annulation. , However, in this manuscript, we have shown for the first time how one can control regiochemical outcome of C–H functionalization/1,3-diyne annulation by choosing heteroatom containing diynes such as 26 and 27 .…”

Section: Resultsmentioning

confidence: 75%

Regioselective Cobalt(II) Catalyzed C–H Functionalization and [3 + 2] Annulation of N-Arylguanidines with 1,3-Diynes

Parihar,

Yadav,

Thirupathi

2024

J. Org. Chem.

View full text Add to dashboard Cite

8-Quinolinyl directed N-arylguanidines were subjected to cobalt(II) catalyzed C–H functionalization/1,3-diyne annulation under mild conditions to afford 40 alkynylated indole guanidines in 34% to 92% yields. The scope of the substrates was explored. The reported procedure is mostly regioselective and tolerates various functional groups in the substrates. The regioselectivity of the reactions was assessed with the aid of multinuclear NMR spectroscopy and X-ray crystallography. Competition and labeling experiments were carried out to support the proposed mechanism.

show abstract

Section: Resultsmentioning

confidence: 75%

Regioselective Cobalt(II) Catalyzed C–H Functionalization and [3 + 2] Annulation of N-Arylguanidines with 1,3-Diynes

Parihar,

Yadav,

Thirupathi

2024

J. Org. Chem.

View full text Add to dashboard Cite

show abstract

Double Chalcogen Bonding Recognition Arrays in Solution

Romito,

Kählig,

Tecilla

et al. 2024

Chemistry A European J

View full text Add to dashboard Cite

N‐substituted pyridino‐based congeners of Ebselen, named here as Pyrselen, incorporating proximal Se and N atoms, undergo dimerization in solution and in the solid state through a dual donor‐acceptor arrangement of chalcogen bonding sites. Dimerization constants were measured within the 15‐50 M–1 range. Computational studies on the dimers depict a notable charge‐transfer contribution to the association, validating Pyrselen as an effective scaffold for designing chalcogen‐bonding‐based recognition motifs. Insert abstract text here.

show abstract

Stable Antiaromatic [16]Triphyrin(2.1.1) with Core Modification: Synthesis Using a 16π Electrocyclic Reaction

Hirai,

Kawazoe,

Yamashita

2024

Chemistry A European J

View full text Add to dashboard Cite

Antiaromatic porphyrinoids have attracted significant attention owing to their unique electronic properties and potential applications. However, synthesis of antiaromatic contracted porphyrinoids is challenging owing to the inherent instability associated with smaller ring sizes. In this study, we report the synthesis and characterization of the first stable trioxa[16]triphyrin(2.1.1), a novel 16π antiaromatic contracted porphyrinoid. We utilized a core modification approach to stabilize the [16]triphyrin(2.1.1). X‐ray crystallographic analysis revealed a nearly planar structure. Electrochemical studies demonstrated reversible oxidation behavior and a small HOMO–LUMO gap, which was consistent with its antiaromatic nature. Chemical oxidation yielded an aromatic [14]triphyrin(2.1.1) dication, highlighting the antiaromaticity–aromaticity switching capability of this system. This synthesis involved the discovery of a key intermediate, dihydrotrioxatriphyrin(2.1.1), which underwent oxidative dehydrogenation to yield the target compound. Theoretical calculations suggested that dihydrotrioxatriphyrin(2.1.1) formed via a rare 16π electrocyclic reaction. The successful synthesis and characterization of this stable trioxa[16]triphyrin(2.1.1) underscores the potential of the core modification strategies for the rational design of novel antiaromatic systems with tunable properties. Moreover, the discovery of the rare 16π electrocyclic reaction advances the understanding of high‐order pericyclic processes and may inspire new synthetic strategies for complex macrocyclic compounds.

show abstract

The Missing Chalcogen Bonding Donor: Strongly Polarized Oxygen of Water

Cited by 6 publications

References 42 publications

Regioselective Cobalt(II) Catalyzed C–H Functionalization and [3 + 2] Annulation of N-Arylguanidines with 1,3-Diynes

Regioselective Cobalt(II) Catalyzed C–H Functionalization and [3 + 2] Annulation of N-Arylguanidines with 1,3-Diynes

Double Chalcogen Bonding Recognition Arrays in Solution

Stable Antiaromatic [16]Triphyrin(2.1.1) with Core Modification: Synthesis Using a 16π Electrocyclic Reaction

Contact Info

Product

Resources

About