139557-96-3Relevant articles and documents
CuSO4-Catalyzed dual annulation to synthesize O, S or N-containing tetracyclic heteroacenes
Kang, Yan-Biao,Qu, Jian-Ping,Shan, Xiang-Huan,Yang, Bo
supporting information, p. 4063 - 4066 (2020/04/20)
In this work, CuSO4 is utilized as a practical redox catalyst for tandem dual annulation in the synthesis of indole-fused tetracyclic heteroacenes, which are important skeletons in both medicinal chemistry and materials chemistry. The preparation of such skeletons in a convenient and efficient manner is in high demand. This method realizes the modular synthesis of benzofuro-, benzothieno-, and indoloindoles from abundant feedstocks such as 2-halobenzyl halides and nitrile derivatives in up to 99% yields, providing a rapid access to diverse indole-fused heteroacenes with biological or optoelectronic properties.
Nickel-Catalyzed Asymmetric Reductive 1,2-Carboamination of Unactivated Alkenes
He, Jun,Xue, Yuhang,Han, Bo,Zhang, Chunzhu,Wang, You,Zhu, Shaolin
supporting information, p. 2328 - 2332 (2020/01/08)
Starting from diverse alkene-tethered aryl iodides and O-benzoyl-hydroxylamines, the enantioselective reductive cross-electrophilic 1,2-carboamination of unactivated alkenes was achieved using a chiral pyrox/nickel complex as the catalyst. This mild, modular, and practical protocol provides rapid access to a variety of β-chiral amines with an enantioenriched aryl-substituted quaternary carbon center in good yields and with excellent enantioselectivities. This process reveals a complementary regioselectivity when compared to Pd and Cu catalysis.
Regioselectivity Influences in Platinum-Catalyzed Intramolecular Alkyne O-H and N-H Additions
Costello, Jeff P.,Ferreira, Eric M.
, p. 9934 - 9939 (2019/12/24)
The steric and electronic drivers of regioselectivity in platinum-catalyzed intramolecular hydroalkoxylation are elucidated. A branch point is found that divides the process between 5-exo and 6-endo selective processes, and enol ethers can be accessed in good yields for both oxygen heterocycles. The main influence arises from an electronic effect, where the alkyne substituent induces a polarization of the alkyne that leads to preferential heteroatom attack at the more electron-deficient carbon. The electronic effects are studied in other contexts, including hydroacyloxylation and hydroamination, and similar trends in directionality are predominant although not uniformly observed.
Palladium-Catalyzed, Norbornene-Mediated, ortho-Amination ipso-Amidation: Sequential C-N Bond Formation
Whyte, Andrew,Olson, Maxwell E.,Lautens, Mark
supporting information, p. 345 - 348 (2018/01/27)
A palladium-catalyzed, norbornene-mediated ortho- and ipso-C-N bond-forming Catellani reaction is reported. This reaction proceeds through a sequential intermolecular amination followed by intramolecular cyclization of a tethered amide. The products, ortho-aminated dihydroquinolinones, were generated in moderate to good yields and are present in bioactive molecules. This work highlights the challenge of competing intra- vs intermolecular palladium-catalyzed processes.
Stereoretentive Intramolecular Glycosyl Cross-Coupling: Development, Scope, and Kinetic Isotope Effect Study
Yi, Duk,Zhu, Feng,Walczak, Maciej A.
supporting information, p. 4627 - 4631 (2018/08/07)
A series of cyclic C-glycosides were synthesized using the palladium-catalyzed stereoretentive intramolecular glycosylation of aryl iodides by employing a bulky phosphine ligand. A variety of functional groups are tolerated in the reaction, and enantioenr
Cu-Catalyzed Enantioselective Ring Opening of Cyclic Diaryliodoniums toward the Synthesis of Chiral Diarylmethanes
Li, Bin,Chao, Zengyin,Li, Chunyu,Gu, Zhenhua
supporting information, p. 9400 - 9403 (2018/07/30)
A Cu-catalyzed enantioselective desymmetrizing ring-opening reaction of six-membered cyclic diaryliodonium salts with carboxylic acids or thioacids is reported for the facile access to chiral diarylmethanes. A Cu/[cyclopropyl bis(oxazoline)] catalyst well
Palladium-catalyzed intermolecular tandem cyclization reaction: a highly regioselective synthesis of functionalized 3H-spiro[isobenzofuran-1,3′-isochroman] scaffolds
Wang, Liang,Li, Xuehu,Tao, Hua,Zhou, Xiang,Lu, Xihong,Du, Wenyue,Jiang, Tingting,Xin, Zhijun,Liang, Jianping
supporting information, p. 2403 - 2410 (2017/03/20)
A highly regioselective synthesis of functionalized 3H-spiro[isobenzofuran-1,3′-isochroman] scaffolds using a novel palladium-catalyzed tandem cyclization reaction is explored. During the reaction process, C-O, C-C and C-O bonds are sequentially formed in one pot via decarboxylative allenylpalladium formation, nucleophilic attack, arylpalladium addition and intramolecular nucleophilic attack.
Pd-Catalyzed Selective Synthesis of Cyclic Sulfonamides and Sulfinamides Using K2S2O5 as a Sulfur Dioxide Surrogate
Konishi, Hideyuki,Tanaka, Hiromichi,Manabe, Kei
, p. 1578 - 1581 (2017/04/13)
A variety of cyclic sulfonamides and sulfinamides could be selectively synthesized under Pd catalysis using haloarenes bearing amino groups and a sulfur dioxide (SO2) surrogate. The amount of base was key in determining the selectivity. Mechanistic studies revealed that sulfinamides were initially formed via an unprecedented formal insertion of sulfur monoxide and were oxidized to sulfonamides in the presence of an iodide ion and DMSO.
Enantioselective allylation of selected ortho-substituted benzaldehydes: A comparative study
Hessler, Filip,Betk, Robert,Kadlkov, Aneta,Belle, Roman,Kotora, Martin
supporting information, p. 7245 - 7252 (2015/01/09)
We report a systematic study of the allylation of ortho-substituted benzaldehydes under catalysis of a Lewis base (N, Ndioxide), a Lewis acid (Keck allylation), and a Bronsted acid. ortho-Halobenzaldehydes were used as the aldehydic substrates, and specia
Intriguing substituent effect in modified Hoveyda-Grubbs metathesis catalysts incorporating a chelating iodo-benzylidene ligand
Barbasiewicz, Michal,Blocki, Krzysztof,Malinska, Maura,Pawlowski, Robert
supporting information, p. 355 - 358 (2013/02/22)
A series of modified Hoveyda-Grubbs catalysts incorporating a chelating iodo-benzylidene ligand were prepared and characterized. The presence of electron-withdrawing ring substituents in the para position to the iodide was found to decrease the catalytic activity, revealing that dissociation of the Ru...I-Ar bond is not the rate-determining step.
