3558-24-5Relevant articles and documents
Trans-Aminoboration across Internal Alkynes Catalyzed by B(C6F5)3 for the Synthesis of Borylated Indoles
Yuan, Kang,Wang, Suning
, p. 1462 - 1465 (2017)
We report here a facile B(C6F5)3 catalyzed trans-aminoboration of internal alkynes, furnishing 3-position borylated indoles at ambient temperature. This reaction proceeds with the breaking of a B-N bond and the formation of N-C and B-C bonds to produce indole and derivatives in one step. It works well for various boron reagents and alkynyl-anilines. The borylated indoles can be further derivatized to give column stable organoboron compounds that can be used for future functionalization.
Structurally-defined direct C-magnesiation and C-zincation of N-heterocyclic aromatic compounds using alkali-metal-mediated metallation
Conway, Ben,Hevia, Eva,Kennedy, Alan R.,Mulvey, Robert E.
, p. 2864 - 2866 (2007)
Demonstrating direct synergic "low polarity metallation", 1-methylindole is C-magnesiated by (TMEDA)2·Na 2MgBu4 and C-zincated by (TMEDA)·Na( tBu)(TMP)Zn(tBu), and 1-methylpyrrole is C-zincated by the same reagent, with all three metal products successfully crystallographically characterised. The Royal Society of Chemistry.
PALLADIUM-PHOSPHINE COMPLEX CATALYZED CROSS-COUPLING REACTION OF 1-METHYL-2-PYRROLYL-MAGNESIUM BROMIDE AND -ZINC CHLORIDE WITH ORGANIC HALIDES
Minato, Akio,Tamao, Kohei,Hayashi, Tamio,Suzuki, Keizo,Kumuda, Makoto
, p. 5319 - 5322 (1981)
1-Methyl-2-pyrrolyl-magnesium bromide and -zinc chloride, which were prepared from 1-methyl-2-pyrrolyllithium with MgBr2 and ZnCl2 respectively, reacted with aryl- and heteroaromatic halides to give the corresponding 2-substituted pyrroles in good to excellent yields in the presence of palladium-phosphine complexes as catalysts.
Synthesis of 2-Substituted Benzothio(seleno)phenes and Indoles via Ag-Catalyzed Cyclization/Demethylation of 2-Alkynylthio(seleno)anisoles and 2-Alkynyldimethylanilines
Cai, Tao,Feng, Chengjie,Shen, Fangqi,Bian, Kejun,Wu, Chunlei,Shen, Runpu,Gao, Yuzhen
supporting information, p. 653 - 656 (2020/12/23)
An Ag-catalyzed cyclization/demethylation of 2-alkynylthio(seleno)anisoles and 2-alkynyldimethylanilines is described and applied for the construction of valuable benzothio(seleno)phenes as well as indoles. Various 2-substituted benzothio(seleno)phenes and indoles were obtained in good to excellent yields under mild reaction conditions with low catalyst loading. An application of this new method is also exemplified with a concise synthesis of a bioactive molecule precursor. Furthermore, a conceivable reaction mechanism is proposed with supports from isotope-exchange experiments.
B(C6F5)3-Catalyzed Electron Donor-Acceptor Complex-Mediated Aerobic Sulfenylation of Indoles under Visible-Light Conditions
Yuan, Wenkai,Huang, Jie,Xu, Xin,Wang, Long,Tang, Xiang-Ying
supporting information, p. 7139 - 7143 (2021/09/14)
An efficient B(C6F5)3-catalyzed aerobic oxidative C-S cross-coupling reaction of thiophenol with indoles was developed, affording a wide range of diaryl sulfides in good yields. An electron donor-acceptor complex between B(C6F5)3 and indoles was formed, facilitating the photoinduced single-electron transfer (SET) from indole substrates to the B(C6F5)3 catalyst. This protocol demonstrates a new reaction model using B(C6F5)3 as a single-electron oxidant.