163105-69-9Relevant articles and documents
'Awaken' aryl sulfonyl fluoride: a new partner in the Suzuki-Miyaura coupling reaction
Ding, Chengrong,Guan, Chenfei,Miao, Huihui,Zhang, Guofu,Zhao, Yiyong
supporting information, p. 3560 - 3564 (2022/03/07)
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
Concatenating Suzuki Arylation and Buchwald–Hartwig Amination by A Sequentially Pd-Catalyzed One-Pot Process—Consecutive Three-Component Synthesis of C,N-Diarylated Heterocycles
Mayer, Laura,Kohlbecher, Regina,Müller, Thomas J. J.
supporting information, p. 15130 - 15134 (2020/10/20)
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.
Total synthesis of (±) aspidostomide B, C, regioisomeric N-methyl aspidostomide D and their derivatives
Hussain, Mulla Althafh,Khan, Faiz Ahmed
supporting information, (2019/08/20)
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.