219540-53-1Relevant academic research and scientific papers
Facile Synthesis of Azahelicenes and Diaza[8]circulenes through the Intramolecular Scholl Reaction
Maeda, Chihiro,Nomoto, Shuichi,Akiyama, Koki,Tanaka, Takayuki,Ema, Tadashi
supporting information, p. 15699 - 15705 (2021/10/12)
Carbazole-based aza[7]helicenes and hetero[9]helicenes were successfully obtained via the intramolecular Scholl reaction of 3,6-bis(biphenyl-2-yl)carbazole congeners, while the reaction of 3,6-bis(naphthylphenyl)-appended carbazole gave a triple helicene via an unexpected simultaneous double aryl rearrangement. DFT calculations suggested that the rearrangement proceeded via an arenium cation intermediate. In addition, the reaction of methoxy-appended substrate gave an azahepta[8]circulene via the concurrent C?C bond formation. These helical dyes showed circularly polarized luminescence. The azahepta[8]circulene was further transformed into deeply saddle-distorted dibenzodiaza[8]circulenes as the first example of its solution-based synthesis and unambiguous structural determination.
Ag-Catalyzed Cyclization of Arylboronic Acids with Elemental Selenium for the Synthesis of Selenaheterocycles
Gao, Wen-Xia,Huang, Xiao-Bo,Liu, Miao-Chang,Wu, Hua-Yue,Zhang, Xue,Zhou, Yun-Bing
supporting information, p. 5639 - 5644 (2020/11/30)
A general method for the synthesis of five-membered and six-membered selenaheterocycles through Ag-catalyzed C?Se bond-forming reaction is reported. This reaction proceeds via intramolecular cyclization of arylboronic acids with selenium powder. Preliminary mechanism studies demonstrate that this transformation involves a selenium-centred radical intermediate. (Figure presented.).
Rh(III)-Catalyzed C-H Activation of Boronic Acid with Aryl Azide
Xu, Shiyang,Huang, Baoliang,Qiao, Guanyu,Huang, Ziyue,Zhang, Zhen,Li, Zongyang,Wang, Peng,Zhang, Zhenhua
supporting information, p. 5578 - 5582 (2018/09/25)
A Rh(III)-catalyzed C-H activation of boronic acid with aryl azide to obtain unsymmetric carbazoles, 1H-indoles, or indolines has been developed. The reaction constructs dual distinct C-N bonds via sp2/sp3 C-H activation and rhodium nitrene insertion. Synthetically, this approach represents an access to widely used carbazole derivatives. The practical application to CBP and unsymmetric TCTA derivatives has also been performed. Mechanistic experiments and DFT calculations demonstrate that a five-membered rhodacycle species is the key intermediate.
Rhodium-Catalyzed Oxidative Annulation of (2-Arylphenyl)boronic Acids with Alkynes: Selective Synthesis of Phenanthrene Derivatives
Nagata, Tomoya,Satoh, Tetsuya,Nishii, Yuji,Miura, Masahiro
supporting information, p. 1707 - 1710 (2016/07/06)
A rhodium-catalyzed annulative coupling of (2-arylphenyl)boronic acids with alkynes has been developed for the facile construction of phenanthrene frameworks. The reaction proceeded without external bases, and dioxygen worked as a terminal oxidant. Deuter
Scyllo-inositol as a convenient protecting group for aryl boronic acids in Suzuki-Miyaura cross-coupling reactions
Kuno, Shinichi,Kimura, Tomoyuki,Yamaguchi, Masanori
, p. 720 - 724 (2014/01/23)
Herein, we report air-and water-stable borate complexes between scyllo-inositol and aryl boronic acids. The complexes were less reactive than free aryl boronic acids under Suzuki-Miyaura cross-coupling reaction conditions; thus, the borate complexes were used as protected boronic acids. Although protecting groups for organoboronic acids are useful in coupling reactions, especially those used to produce π-conjugated molecules, only a few reports describing the use of protecting groups for boronic acids have been published. The proposed unique structural borate complex provides a novel protective method for aryl boronic acids.
Poly-orthophenylenes: Synthesis by Suzuki coupling and solid state helical structures
Blake, Alexander J.,Cooke, Paul A.,Doyle, Kevin J.,Gair, Susan,Simpkins, Nigel S.
, p. 9093 - 9096 (2007/10/03)
The preparation of ortho-polyphenylene oligomers, having 3-9 rings, using a rational Suzuki coupling stretegy, has been achieved, and a helical structure determined for a number of these products by X-ray crystallography.
