59099-79-5Relevant articles and documents
Catalyst-Free Formal Thioboration to Synthesize Borylated Benzothiophenes and Dihydrothiophenes
Faizi, Darius J.,Davis, Ashlee J.,Meany, Fiach B.,Blum, Suzanne A.
, p. 14286 - 14290 (2016)
The first ring-forming thioboration reaction of C?C π bonds is reported. This catalyst-free method proceeds in the presence of a commercially available external electrophilic boron source (B-chlorocatecholborane) in good to high yields. The method is scalable and tolerates a variety of functional groups that are intolerant of other major borylation methods. The resulting borylated benzothiophenes participate in a variety of in situ derivatization reactions, showcasing that these borylated intermediates do not need to be isolated prior to downstream functionalization. This methodology has been extended to the synthesis of borylated dihydrothiophenes. Mechanistic experiments suggest that the operative mechanistic pathway is through boron-induced activation of the alkyne followed by electrophilic cyclization, as opposed to S?B σ bond formation, providing a mechanistically distinct pathway to the thioboration of C?C π bonds.
Synthesis of non-glutamate-type pyrrolo[2,3-d]pyrimidines via direct aminocarbonylation of aryl halides using solid Co2(CO)8 as a CO source and their antibacterial activity
Selvakumar, Balaraman,Elango, Kuppanagounder P.
, p. 230 - 234 (2017)
The synthesis of pyrrolo[2,3-d]pyrimidine derivatives by direct aminocarbonylation was demonstrated using solid Co2(CO)8 as a CO source in an autoclave at elevated temperature by reacting an aryl halide scaffold with a variety of amines. Using this method, 12 non-glutamate-type pyrrolo[2,3-d]pyrimidine analogues were prepared. Some compounds exhibited antibacterial activity against both Gram-positive and Gram-negative bacteria.
A General Protocol for Robust Sonogashira Reactions in Micellar Medium
Jakobi, Markus,Gallou, Fabrice,Sparr, Christof,Parmentier, Michael
, (2019/03/13)
A robust and general protocol for a sustainable copper-free Sonogashira cross coupling under micellar aqueous reaction conditions with high turnover was developed. By using the commercially available catalyst CataCXium A Pd G3 and THF as co-solvent, vario
Asymmetric Synthesis of Fused Bicyclic N,O- and O,O-Acetals via Cascade Reaction by Gold(I)/N,N′-Dioxide-Nickel(II) Bimetallic Relay Catalysis
Hu, Bowen,Li, Jun,Cao, Weidi,Lin, Qianchi,Yang, Jian,Lin, Lili,Liu, Xiaohua,Feng, Xiaoming
supporting information, p. 2831 - 2835 (2018/08/17)
An efficient catalytic asymmetric cyclization/inverse-electron-demand hetero-Diels-Alder cascade reaction of β,γ-unsaturated α-ketoesters with alkyl amides or alcohols were accomplished. The process was based on the utilization bimetallic catalyst system with achiral gold(I) catalyst and chiral N,N′-dioxide/Ni(II) catalyst, delivering a variety of fused bicyclic N,O-acetals or O,O-acetals in up to 99% yield and 99% ee with >19:1 dr under mild reaction conditions. Based on the control experiments and previous studies, a possible reaction pathway of bimetallic relay catalysis cascade reactions was presented. (Figure presented.).
Accessing alternative reaction pathways of the intermolecular condensation between homo-propargyl alcohols and terminal alkynes through divergent gold catalysis
Smith, Courtney A.,Motika, Stephen E.,Wojtas, Lukasz,Shi, Xiaodong
supporting information, p. 2315 - 2318 (2017/02/23)
An intermolecular condensation of alkynols and terminal alkynes is reported. Using IPrAuNTf2, an efficient Au-catalyzed cyclization-alkynylation strategy furnishes (2-arylalkynyl) cyclic ethers in moderate to excellent yields (up to 94%). This strategy is extended to the synthesis of functionalized 2,3-dihydrooxepines via the sequential Au-catalyzed ring expansion of the cyclic ether substrates.
Rhodium(III)-catalyzed oxidative bicyclization of 4-arylbut-3-yn-1-amines with internal alkynes through C-H functionalization
Pi, Rui,Zhou, Ming-Bo,Yang, Yuan,Gao, Cai,Song, Ren-Jie,Li, Jin-Heng
supporting information, p. 13550 - 13553 (2015/09/01)
A new Rh(III)-catalyzed oxidative bicyclization through C-H functionalization is presented. This reaction allows the selective assembly of diverse benzo[g]indoles from 4-arylbut-3-yn-1-amines and internal alkynes via a sequence of aromatic C(sp2)-H functionalization, cyclodimerization and nucleophilic cyclization.
Synthesis of planar-chiral paracyclophanes via samarium(II)-catalyzed intramolecular pinacol coupling
Ueda, Tsuyoshi,Kanomata, Nobuhiro,Machida, Hajime
, p. 2365 - 2368 (2007/10/03)
(Chemical Equation Presented) A series of [n]jparacyclophanediols (n = 8-12) was synthesized by samarium-catalyzed pinacol coupling for their ansa-bridge formation. Enantiomerically pure [n]jparacyclophane esters were derived from the diols in a several steps via chiral resolution (for n = 10) or via crystallization-induced asymmetric transformation (for n = 11) by using amino alcohol auxiliaries and their selective cleavages.
