16538-48-0Relevant articles and documents
Highly stereo and chemoselective iron-catalyzed alkenylation of organomagnesium compounds
Cahiez, Gerard,Avedissian, Hovsep
, p. 1199 - 1205 (1998)
In the presence of Fe(acac)3, Grignard reagents react readily with alkenyl halides (X = I, Br or Cl) in a THF/NMP mixture to give the cross-coupling products in high yields with an excellent stereoselectivity (≤99.5%). The scope of the reaction is very broad since a vast array of functional groups are tolerated (esters, nitriles, aromatic or aliphatic halides and even ketones). The procedure reported herein is an interesting alternative to the classical Pd- or Ni-catalyzed reactions, especially for preparative organic chemistry.
Vinylic Organoboranes. 6. A General Synthesis of (E)-Disubstituted Alkenes or Ketones via the (E)-(1-Substituted-1-alkenyl)boronic Esters
Brown, Herbert C.,Basavaiah, D.,Kulkarni, Surendra U.,Lee, Hsiupu D.,Negishi, Ei-ichi,Katz, Jean-Jacques
, p. 5270 - 5276 (1986)
Development of a general stereospecific synthesis of (E)-disubstituted alkenes utilizing a variety of hydroborating agents such as monohaloborane, thexylborane, thexylchloroborane, and dibromoborane is discussed.Hydroboration of 1-halo-1-alkynes with dial
A stereoselective synthesis of 1,2-disubstituted alkenyl selenides via hydroboration-iodination of internal alkylselenoacetylenes with dicyclohexylborane
Yang, De Yu,Huang, Xian
, p. 139 - 143 (1996)
Selenoalkenyldicyclohexylboranes, prepared conveniently via hydroboration of internal alkylselenoacetylenes with dicyclohexylborane followed by iodination under basic conditions, produce cis/trans 1,2-disubstituted alkenyl selenides (1 and 2), which provide a general method for synthesis of cis/trans disubstituted alkenyl selenides containing a cyclohexyl group.
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Zweifel,G. et al.
, p. 3652 - 3653 (1967)
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1-Methyl-1H-tetrazol-5-yl (MT) sulfones in the Julia-Kocienski olefination: Comparison with the PT and the TBT sulfones
Ando, Kaori,Kawano, Daiki,Takama, Daiki,Semii, Yutaka
, p. 1566 - 1569 (2019/05/22)
The stability and the stereoselectivity of newly prepared n-pentyl 1-methyl-1H-tetrazol-5-yl (MT) sulfone 1a in the Julia-Kocienski reactions were compared with those of the PT sulfone 1b and the TBT sulfone 1c. The improved stability of the anion derived from the n-pentyl MT sulfone 1a enhanced the efficiency of the olefination reactions and gave higher yields of the product alkenes 3 compared with the PT sulfone 1b. Especially high E-selectivity and high yields were obtained from the reaction with aromatic aldehydes and α,β-unsaturated aldehydes. The selectivity of 1a was not so sensitive to the change of base counter ion compared with the PT sulfone 1b. The reaction of the MT sulfones having either ethyl or a longer alkyl chain also gave E-alkenes selectively in high yields.
Synthesis of E-Alkyl Alkenes from Terminal Alkynes via Ni-Catalyzed Cross-Coupling of Alkyl Halides with B-Alkenyl-9-borabicyclo[3.3.1]nonanes
Di Franco, Thomas,Epenoy, Alexandre,Hu, Xile
supporting information, p. 4910 - 4913 (2015/10/12)
The first Ni-catalyzed Suzuki-Miyaura coupling of alkyl halides with alkenyl-(9-BBN) reagents is reported. Both primary and secondary alkyl halides including alkyl chlorides can be coupled. The coupling method can be combined with hydroboration of termina
