67364-02-7Relevant academic research and scientific papers
Evidence for Simultaneous Dearomatization of Two Aromatic Rings under Mild Conditions in Cu(I)-Catalyzed Direct Asymmetric Dearomatization of Pyridine
Buchwald, Stephen L.,Gribble, Michael W.,Liu, Richard Y.
, p. 11252 - 11269 (2020)
Bis(phosphine) copper hydride complexes are uniquely able to catalyze direct dearomatization of unactivated pyridines with carbon nucleophiles, but the mechanistic basis for this result has been unclear. Here we show that, contrary to our initial hypothes
Copper-Catalyzed Asymmetric Radical 1,2-Carboalkynylation of Alkenes with Alkyl Halides and Terminal Alkynes
Dong, Xiao-Yang,Cheng, Jiang-Tao,Zhang, Yu-Feng,Li, Zhong-Liang,Zhan, Tian-Ya,Chen, Ji-Jun,Wang, Fu-Li,Yang, Ning-Yuan,Ye, Liu,Gu, Qiang-Shuai,Liu, Xin-Yuan
supporting information, p. 9501 - 9509 (2020/05/18)
A copper-catalyzed intermolecular three-component asymmetric radical 1,2-carboalkynylation of alkenes has been developed, providing straightforward access to diverse chiral alkynes from readily available alkyl halides and terminal alkynes. The utilization of a cinchona alkaloid-derived multidentate N,N,P-ligand is crucial for the efficient radical generation from mildly oxidative precursors by copper and the effective inhibition of the undesired Glaser coupling side reaction. The substrate scope is broad, covering (hetero)aryl-, alkynyl-, and aminocarbonyl-substituted alkenes, (hetero)aryl and alkyl as well as silyl alkynes, and tertiary to primary alkyl radical precursors with excellent functional group compatibility. Facile transformations of the obtained chiral alkynes have also been demonstrated, highlighting the excellent complementarity of this protocol to direct 1,2-dicarbofunctionalization reactions with C(sp2/sp3)-based reagents.
Furanodendralenes
Fallon, Thomas,Willis, Anthony C.,Paddon-Row, Michael N.,Sherburn, Michael S.
, p. 3185 - 3193 (2014/05/06)
An examination of Diels-Alder reactions of furan-containing analogues of dendralenes has revealed complex and fascinating reaction sequences, which chart the inherent site and stereoselectivity of these processes and give rapid access to structures of hig
Cross coupling in water: Suzuki-Miyaura vinylation and difluorovinylation of arylboronic acids
Pschierer, Jan,Peschek, Natalie,Plenio, Herbert
experimental part, p. 636 - 642 (2010/08/20)
A general and efficient protocol for the Suzuki-Miyaura coupling of aryl boronic acids with vinylmesylate or difluorovinylmesylate or Cl 2CCF2 in water or water/n-butanol is reported, utilizing Na2PdCl4 (1 mol%) and a highly water-soluble fluorenylphosphine (CataCXium F sulf).
Synthesis of α-heteroarylpropanoic acid via asymmetric hydroformylation catalyzed by Rh(I)-(R,S)-BINAPHOS and the subsequent oxidation
Tanaka, Ryo,Nakano, Koji,Nozaki, Kyoko
, p. 8671 - 8676 (2008/03/12)
(Chemical Equation Presented) The asymmetric hydroformylation of vinyl heteroarenes (vinylfurans and vinylthiophenes) was investigated by using Rh(I)-BINAPHOS derivatives as a catalyst. The hydroformylation of vinylthiophenes 1 gave the corresponding branched aldehydes 2 with high enantiopurities as major products. Oxidation of the aldehydes 2 successfully afforded α-heteroarylpropanoic acids 4 in good yields. In addition, the aldehydes 2 were reduced to alcohols 5 without loss of enantiomeric excess.
Hydrazines and azides via the metal-catalyzed hydrohydrazination and hydroazidation of olefins
Waser, Jerome,Gaspar, Boris,Nambu, Hisanori,Carreira, Erick M.
, p. 11693 - 11712 (2007/10/03)
The discovery, study, and implementation of the Co- and Mn-catalyzed hydrohydrazination and hydroazidation reactions of olefins are reported. These reactions are equivalent to direct hydroaminations of C-C double bonds with protected hydrazines or hydrazoic acid but are based on a different concept in which the H and the N atoms come from two different reagents, a silane and an oxidizing nitrogen source (azodicarboxylate or sulfonyl azide). The hydrohydrazination reaction using di-tert-butyl azodicarboxylate is characterized by its ease of use, large functional group tolerance, and broad scope, including mono-, di-, tri-, and tetrasubstituted olefins. Key to the development of the hydroazidation reaction was the use of sulfonyl azides as nitrogen sources and the activating effect of tert-butyl hydroperoxide. The reaction was found to be efficient for the functionalization of mono-, di-, and trisubstituted olefins, and only a few functional groups are not tolerated. The alkyl azides obtained are versatile intermediates and can be transformed to the free amines or triazoles without isolation of the azides. Preliminary mechanistic investigations suggest a rate-limiting hydrocobaltation of the alkene, followed by an amination reaction. Radical intermediates cannot be ruled out and may be involved.
Teubrevin G and teubrevin H: The first total syntheses of rearranged neo-clerodanes including solutions to the problems of chirality merger and furan ring assembly
Paquette,Efremov
, p. 4492 - 4501 (2007/10/03)
Total syntheses of teubrevins G (2) and H (3) are described. The reported strategy relies on a highly regioselective cycloaddition-fragmentation approach to the construction of a 2,3,4-trisubstituted furan and features efficient ring-closing metathesis ch
A new route to 2,7- and 7-functionalized labdanes
Hersel, Ulrich,Steck, Melanie,Seifert, Karlheinz
, p. 1609 - 1615 (2007/10/03)
A new route for the synthesis of 2,7- and 7-functionalized labdanes starts from (R)-carvone (1). 11-Nordrim-7-en-9-one (15) is an appropriate starting material for the total synthesis of hispanone (21), a biologically active furolabdane isolated from the
A REGIOSPECIFIC SYNTHESIS OF CARBOSUBSTITUTED HETEROAROMATIC DERIVATIVES VIA Pd-CATALYZED CROSS COUPLING
Negishi, Ei-ichi,Luo, Fen-Tair,Frisbee, Roger,Matsushita, Hajime
, p. 117 - 122 (2007/10/02)
The Pd-catalyzed cross-coupling reaction of either heteroarylzinc derivatives with unsaturated organic halides or heteroaryl halides with organometallic reagents containing Zn or Al can produce cleanly and regiospecifically the corresponding carbo-substituted heteroatomic compounds in high yields.
