- 'Awaken' aryl sulfonyl fluoride: a new partner in the Suzuki-Miyaura coupling reaction
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An example of the activation of the -SO2F group, which is traditionally considered a stable group even in the presence of a transition metal, is described using a novel partner in the Suzuki-Miyaura coupling reaction catalyzed by Pd(OAc)2 and Ruphos as ligands. The products showed good to outstanding yields and broad functional group compatibility under optimal conditions. The sequential synthesis of non-symmetric terphenyls and the gram grade process highlight the approach's synthetic utility. DFT calculations have shown that Pd0 prefers to insert between C-S bonds rather than S-F bonds. This journal is
- Ding, Chengrong,Guan, Chenfei,Miao, Huihui,Zhang, Guofu,Zhao, Yiyong
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supporting information
p. 3560 - 3564
(2022/03/07)
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- Cp?Co(III)-Catalyzed enantioselective hydroarylation of unactivated terminal alkenes via C-H activation
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Enantioselective hydroarylation of unactivated terminal akenes constitutes a prominent challenge in organic chemistry. Herein, we reported a Cp*Co(III)-catalyzed asymmetric hydroarylation of unactivated aliphatic terminal alkenes assisted by a new type of tailor-made amino acid ligands. Critical to the chiral induction was the engaging of a novel noncovalent interaction (NCI), which has seldomly been disclosed in the C-H activation area, arising from the molecular recognition among the organocobalt(III) intermediate, the coordinated alkene, and the well-designed chiral ligand. A broad range of C2-alkylated indoles were obtained in high yields and excellent enantioselectivities. DFT calculations revealed the reaction mechanism and elucidated the origins of chiral induction in the stereodetermining alkene insertion step.
- Fan, Jun,Hong, Xin,Liu, Lei,Liu, Yan-Hua,Shi, Bing-Feng,Xie, Pei-Pei,Zhang, Zhuo-Zhuo
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supporting information
p. 19112 - 19120
(2021/11/26)
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- Concatenating Suzuki Arylation and Buchwald–Hartwig Amination by A Sequentially Pd-Catalyzed One-Pot Process—Consecutive Three-Component Synthesis of C,N-Diarylated Heterocycles
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The concatenation of Suzuki coupling and Buchwald-Hartwig amination in a consecutive multicomponent reaction opens a concise, modular and efficient one-pot approach to diversely functionalized heterocycles, as exemplified for 3,10-diaryl 10H-phenothiazines, 3,9-diaryl 9H-carbazoles, and 1,5-diaryl 1H-indoles, in high yields starting from simple staring materials. Moreover, this one-pot reaction is a sequentially palladium-catalyzed process that does not require additional catalyst loading after the first coupling step.
- Mayer, Laura,Kohlbecher, Regina,Müller, Thomas J. J.
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supporting information
p. 15130 - 15134
(2020/10/20)
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- Synthesis of heterobiaryls via Suzuki-Miyaura coupling reaction of potassium aryltrifluoroborates with heteroaryl halides in aqueous systems
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A variety of heterobiaryl compounds have been synthesized by the Suzuki-Miyaura coupling reactions of heteroaryl halides with potassium aryltrifluoroborates. Pd (OAc)2 was found to be highly efficient for the Suzuki-Miyaura coupling reactions of various heteroaryl halides with potassium aryltrifluoroborates in aqueous systems, delivering the corresponding heterobiaryl compounds in good to excellent yields.
- Liu, Leifang,Zhao, Kai,Li, Wenbo,Liu, Mingli,Chen, Yuting,Dong, Yan
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- Total synthesis of (±) aspidostomide B, C, regioisomeric N-methyl aspidostomide D and their derivatives
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A full account of the total synthesis of aspidostomide B, C, their analogues and our synthetic efforts towards the synthesis of aspidostomide D, which led to the synthesis of regioisomeric N-methyl aspidostomide D, its analogues via epoxide opening strategy is presented. The synthesis of regioisomeric N-methyl aspidostomide D involves an efficient, five-step sequence, with 36.3% overall yield, starting from 3,4,5-tribromo-1H-pyrrole-2-carboxylic acid. The key features of this protocol are intramolecular cyclization, dehydration, oxidation, and a Lewis acid-mediated regioselective epoxide ring opening by C-3 position of 2,5-dibromo-1H-indole to furnish the title compounds.
- Hussain, Mulla Althafh,Khan, Faiz Ahmed
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supporting information
(2019/08/20)
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- INDOLE DERIVATIVES USEFUL AS GLUCAGON RECEPTOR ANTAGONISTS
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The present invention is directed to indole derivatives, pharmaceutical compositions containing them and their use in the treatment and/or prevention of disorders and conditions ameliorated by antagonizing one or more glucagon receptors, including for example metabolic diseases such as Type II diabetes mellitus and obesity.
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Paragraph 0228-0229
(2018/03/24)
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- Using 'biased-privileged' scaffolds to identify lysine methyltransferase inhibitors
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Methylation of histones by lysine methyltransferases (KMTases) plays important roles in regulating chromatin function. It is also now clear that improper KMTases activity is linked to human diseases, such as cancer. We report an approach that employs drug
- Kashyap, Sudhir,Sandler, Joel,Peters, Ulf,Martinez, Eduardo J.,Kapoor, Tarun M.
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supporting information
p. 2253 - 2260
(2014/04/17)
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- Microwave-promoted Suzuki reactions of aryl chlorides in aqueous media
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(Chemical Equation Presented) The microwave-promoted Suzuki coupling reaction of aryl chlorides with boronic acids performed in an aqueous media was studied using the air- and moisture-stable catalyst POPd2 (dihydrogen di-μ-chlorodichlorobis(di-test-butylphosphinito-κP)dipalladate (2-)). This catalyst system under microwave conditions (150°C, 15 min) provided coupled products with yields ranging from 64% to 99%. This method tolerated a variety of substituents and sterically hindered substrates.
- Miao, Guobin,Ye, Ping,Yu, Libing,Baldino, Carmen M.
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p. 2332 - 2334
(2007/10/03)
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