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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Gram-Scale, Cheap, and Eco-Friendly Iron-Catalyzed Cross-Coupling between Alkyl Grignard Reagents and Alkenyl or Aryl Halides
Cahiez, Gérard,Lefèvre, Guillaume,Moyeux, Alban,Guerret, Olivier,Gayon, Eric,Guillonneau, Lo?c,Lefèvre, Nicolas,Gu, Qinzhuo,Zhou, Edouard
supporting information, p. 2679 - 2683 (2019/04/30)
A new robust methodology for gram-scale iron-catalyzed cross-coupling between alkyl Grignard reagents and alkenyl or aryl halides is developed. This method does not require toxic additives such as NMP or expensive ligands. Its efficiency relies on the use of simple alkoxide magnesium salts as additives. On the basis of these results, a new procedure for one-pot synthesis of substituted benzamides from chloroesters is also proposed.
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