92496-19-0Relevant articles and documents
Heteroatom-Guided, Palladium-Catalyzed, Site-Selective C-H Arylation of 4H-Chromenes: Diastereoselective Assembly of the Core Structure of Myristinin B through Dual C-H Functionalization
Pawar, Govind Goroba,Tiwari, Virendra Kumar,Jena, Himanshu Sekhar,Kapur, Manmohan
supporting information, p. 9905 - 9911 (2015/06/30)
A highly site-selective, heteroatom-guided, palladium-catalyzed direct arylation of 4H-chromenes is reported. The C-H functionalization is driven not only by the substituents and structure of the substrate but also by the coupling partner being used. The diastereoselective assembly of the core structure of Myristinin B has been achieved by using a dual C-H functionalization strategy for regioselective direct arylation.
Nickel-catalyzed cross-coupling of chromene acetals and boronic acids
Graham, Thomas J. A.,Doyle, Abigail G.
supporting information; experimental part, p. 1616 - 1619 (2012/06/05)
A modular and highly efficient protocol for the synthesis of 2-aryl- and heteroaryl-2H-chromenes is described. Under base-free conditions, readily accessible 2-ethoxy-2H-chromenes undergo Csp3-O activation and C sp3-C bond formation in the presence of an inexpensive nickel catalyst and boronic acids. This new strategy enables broad access to 2-substituted-2H-chromenes and has been applied to the late-stage incorporation of complex molecules, including the pharmaceuticals loratidine and indomethacin methyl ester.
PtIV-catalyzed cyclization of arene-alkyne substrates via intramolecular electrophilic hydroarylation
Pastine, Stefan J.,Youn, So Won,Sames, Dalibor
, p. 1055 - 1058 (2007/10/03)
(Figure presented) We herein report that PtCl4 has proven to be a hydroarylation catalyst with an efficiency and substrate scope superior to previously known methods. This catalyst demonstrated consistent performance with arene-yne substrates of diverse structural features, including propargyl ethers, propargylamines, and alkynoate esters, providing good to excellent yields of the 6-endo products (chromenes, dihydroquinolines, and coumarins). In contrast, Pt(II), Pd(II), and Ga(III) salts were shown to be sensitive to the substitution on the alkyne moiety.
Pt(IV)-catalyzed cyclization of arene-alkyne substrates via C-H bond functionalization
Pastine, Stefan J.,Youn, So Won,Sames, Dalibor
, p. 8859 - 8868 (2007/10/03)
We herein report that PtCl4 has proven to be a hydroarylation catalyst with an efficiency and substrate scope superior to previously known methods. This catalyst demonstrated consistent performance with arene-yne substrates of diverse structural features, including propargyl ethers, propargylamines, and alkynoate esters, providing good to excellent yields of the 6-endo products (chromenes, dihydroquinolines, and coumarins). In contrast, Pt(II), Pd(II), and Ga(III) salts were shown to be sensitive to the substitution on the alkyne moiety. PtCl4 is compatible with both terminal and disubstituted alkynes, as well as with various functionalities on the arene ring, including methyl, methoxyl, hydroxyl, protected amine, and halide.
Novel and Efficient Synthesis of Rotenoids via Intramolecular Radical Arylation
Ahmad-Junan, S. Asiah,Amos, Peter C.,Whiting, Donald A.
, p. 539 - 546 (2007/10/02)
Treatment of the iodoarylchromenes 22 with palladium acetate gave the tetracyclic compounds 23 via a formal but stereochemically disallowed Heck reaction; a crystalline intermediate palladium species 25 (X-ray analysis) was isolated.The method was employe
Palladium-catalysed Intramolecular Arylation: a New Synthesis of Munduserone
Amos, Peter C.,Whiting, Donald A.
, p. 510 - 511 (2007/10/02)
Treatment of the aryl iodides (11) with palladium acetate gave the teracyclic stilbenes (13) via a formal but stereochemically disallowed Heck reaction; the method was exploited to synthesise (+/-)-munduserone (21).
