[reaction: see text] The ortho position of the aromatic ring of pyridyl group-substituted aromatic compounds is directly arylated or alkenylated with organic halides in the presence of a catalytic amount of a ruthenium(II)-phosphine complex.
The skeletal reorganization of 1,6-enynes into 1-vinylcyclopentenes was catalyzed by a cationic platinum complex under extremely mild conditions. The unusual rearrangement of the carbon skeleton, involving the cleavage of both the double and triple carbon-carbon bonds, was observed in certain cases and confirmed by 13 C-and 2 H-labeling experiments. Reaction mechanisms describing the rearrangement of carbocations are proposed.
New luminescent compounds consisting of 10H-phenoxaboryl group as an electron-accepting unit and carbazole (9), 9,9dimethylacridane (10), or phenoxazine (11) as an electron-donating unit have been synthesized. Compounds 10 and 11 showed thermally activated delayed fluorescence (TADF) with light blue and green emissions, respectively, with very high PL quantum yields (PLQYs), however, compound 9 exhibited only a prompt emission and no delayed component. Photoluminescence studies and quantum chemical calculation based on density functional theory (DFT) and timedependent density functional theory (TD-DFT) revealed that in comparison with compound 9, HOMO and LUMO for compounds 10 and 11 are well separated, resulting in lowering ∆EST and effective reverse intersystem crossing (RISC) between a lowest triplet excited state (T1) and a lowest singlet excited state (S1). Organic light-emitting diodes (OLEDs) using compounds 10 and 11 exhibited light blue and green emissions with very good maximum ηext of 15.1% and 22.1%, respectively.
The ortho position of the aromatic ring in 2-aryloxazolines and 2-arylimidazolines is selectively arylated and alkenylated with organic halides in the presence of a ruthenium(II)-phosphine complex. In the case of unsubstituted and para-substituted phenyloxazolines, 1:2 coupled products were obtained preferentially, while 1:1 coupled products were obtained in the case of meta-substituted phenyloxazolines and N-acylarylimidazolines. The reaction is proposed to proceed via the generation of an organoruthenium intermediate, formed by oxidative addition of the organic halide, and ortho-ruthenation directed by the coordination of the 2-oxazolinyl or 2-imidazolinyl group to the ruthenium center.
Direct arylation of thiophenes and benzothiophenes with aryltrimethylsilanes was effectively catalyzed by PdCl(2)(MeCN)(2) in the presence of CuCl(2) as an oxidant. The reaction preferentially occurred at the β-position of both thiophenes and benzothiophenes.
The ortho position of the aromatic ring of pyridyl groupsubstituted aromatic compounds was directly arylated with tetraarylstannanes in the presence of a catalytic amount of a rhodium(I)-phosphine complex.
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