133165-98-7Relevant academic research and scientific papers
The Selective Cross-Coupling of Secondary Alkyl Zinc Reagents to Five-Membered-Ring Heterocycles Using Pd-PEPPSI-IHeptCl
Atwater, Bruce,Chandrasoma, Nalin,Mitchell, David,Rodriguez, Michael J.,Pompeo, Matthew,Froese, Robert D. J.,Organ, Michael G.
supporting information, p. 9502 - 9506 (2015/08/11)
The ability to cross-couple secondary alkyl centers is fraught with a number of problems, including difficult reductive elimination, which often leads to β-hydride elimination. Whereas catalysts have been reported that provide decent selectivity for the expected (non-rearranged) cross-coupled product with aryl or heteroaryl oxidative-addition partners, none have shown reliable selectivity with five-membered-ring heterocycles. In this report, a new, rationally designed catalyst, Pd-PEPPSI-IHeptCl, is demonstrated to be effective in selective cross-coupling reactions with secondary alkyl reagents across an impressive variety of furans, thiophenes, and benzo-fused derivatives (e.g., indoles, benzofurans), in most instances producing clean products with minimal, if any, migratory insertion for the first time. A wide variety of five-membered-ring heterocycles were successfully cross-coupled to secondary alkyl zinc reagents with the new precatalyst Pd-PEPPSI-IHeptCl, which features a bulky N-heterocyclic carbene ligand. This catalyst suppresses migratory-insertion (rearrangement) pathways, and the desired products are thus formed with high selectivity.
Dinuclear iron complex-catalyzed cross-coupling of primary alkyl fluorides with aryl grignard reagents
Mo, Zhenbo,Zhang, Qiang,Deng, Liang
, p. 6518 - 6521 (2012/10/29)
Iron-catalyzed cross-coupling of nonactivated primary alkyl fluorides with aryl Grignard reagents has been achieved by using the low-coordinate dinuclear iron complex [(IPr2Me2)Fe(μ2-NDipp) 2Fe(IPr2Me2)] as the catalyst. This iron-catalyzed C(sp3)-F bond arylation reaction is applicable to a variety of aryl Grignard reagents and primary alkyl fluorides. The product pattern suggests the involvement of a radical-type mechanism for its C-F bond scission step.
Tandem synthesis of 2,3-dihydro-4-iminoquinolines via three-component alkyne-imine metathesis
Saito, Akio,Kasai, Jun,Konishi, Tomoyo,Hanzawa, Yuji
supporting information; scheme or table, p. 6980 - 6982 (2010/11/24)
In the absence of any catalysts, ortho-alkynylanilines react with aldehydes and amines in HFIP to form trans-2,3-disubstituted 2,3-dihydro-4- iminoquinolines in a complete trans-selective manner via the three-component alkyne-imine metathesis.
Platinum-catalyzed consecutive C-N bond formation-[1,3] shift of carbamoyl and ester groups
Nakamura, Itaru,Sato, Yusuke,Konta, Sayaka,Terada, Masahiro
supporting information; experimental part, p. 2075 - 2077 (2009/09/05)
The reaction of ortho-alkynylphenylureas 1 having a carbamoyl group attached to the nitrogen atom proceeded in the presence of catalytic amounts of PtI4, affording corresponding indole-3-carbamides 2 in moderate to high yields. In addition, the platinum-catalyzed cyclization of ortho-alkynylphenyl carbamates 3 afforded corresponding indole-3-carboxylates 4 in good yields. The present reaction proceeds through the intramolecular addition of carbon-nitrogen bonds to triple bonds, the so-called carboamination.
Intramolecular C-N bond addition of amides to alkynes using platinum catalyst
Shimada, Tomohiro,Nakamura, Itaru,Yamamoto, Yoshinori
, p. 10546 - 10547 (2007/10/03)
The intramolecular aminoacylation of alkynes using ortho-alkynylacetanilides proceeds in very high yields in the presence of PtCl2 catalyst. This reaction provides not only a useful procedure for synthesizing 2,3-disubstituted indoles at once from ortho-alkynylaniline derivatives, but also an interesting mechanistic aspect; the intramolecular C-N bond addition of amides to alkynes takes place readily in the presence of Pt(II) catalyst. Copyright
Mercury in Organic Chemistry. 26. Synthesis of Heterocycles via Intramolecular Solvomercuration of Aryl Acetylenes
Larock, Richard C.,Harrison, L. Wayne
, p. 4218 - 4227 (2007/10/02)
A number of ortho substituted aryl acetylenes, o-CH3XC6H4YCCR (X=O, S, CO2; Y=-, CO), have been observed to undergo facile intramolecular solvomercuration with mercuric acetate in acetic acid to afford the corresponding benzofuran, benzothiophene, isocoumarin, and chromone organomercuric chlorides, after aqueous sodium chloride workup.The aryl acetylenes m-XC6H4YCH2CCR (X=H, Y=O, R=CH3; X=CH3O, Y=CH2, R=n-C3H7) undergo similar cyclizations to yield mercurated 2H-1-benzopyrans and 1,2-dihydronaphthalenes.The mercuration and subsequent carbonylation of o-R1OC6H4CCR2 1=Si(t-Bu)Me2, R2=CH3; R1=CH3, R2=o-C6H4OCH3> has provided a new approach to the coumarin and coumestan ring systems.
