63213-07-0Relevant articles and documents
Copper-Catalyzed Reductive Cross-Coupling of Nonactivated Alkyl Tosylates and Mesylates with Alkyl and Aryl Bromides
Liu, Jing-Hui,Yang, Chu-Ting,Lu, Xiao-Yu,Zhang, Zhen-Qi,Xu, Ling,Cui, Mian,Lu, Xi,Xiao, Bin,Fu, Yao,Liu, Lei
, p. 15334 - 15338 (2016/02/18)
A copper-catalyzed reductive cross-coupling reaction of nonactivated alkyl tosylates and mesylates with alkyl and aryl bromides was developed. It provides a practical method for efficient and cost-effective construction of aryl-alkyl and alkyl-alkyl C=C bonds with stereocontrol from readily available substrates. When used in an intramolecular fashion, the reaction enables convenient access to various substituted carbo- or heterocycles, such as 2,3-dihydrobenzofuran and benzochromene derivatives.
Formation of cyclopropanes by the reductive coupling of 1,3-dihalides promoted by titanocene(II) species
Takeda, Takeshi,Shimane, Keiko,Fujiwara, Tooru,Tsubouchi, Akira
, p. 290 - 291 (2007/10/03)
The treatment of various 1,3-dihalides including the ones bearing an ester group with the titanocene(II) species produced cyclopropanes in good yields. The reaction of dihalides possessing two secondary halogens proceeded stereoselectively to afford trans
Scope and utility of a new soluble copper catalyst [CuBr-LiSPh-LiBr-THF]: A comparison with other copper catalysts in their ability to couple one equivalent of a Grignard reagent with an alkyl sulfonate
Burns, Dennis H.,Miller, Jeffrey D.,Chan, Ho-Kit,Delaney, Michael O.
, p. 2125 - 2133 (2007/10/03)
A mixture of equal amounts of CuBr-SMe2, LiBr, and LiSPh in THF at 0°C furnished a new soluble copper catalyst that was highly efficient at coupling primary, secondary, tertiary, aryl, vinyl, and allylic Grignard reagents to primary tosylates and primary Grignard reagents to secondary tosylates and mesylates, all with the use of only 1 equiv of Grignard reagent. The new catalyst was shown to be much more reactive than copper catalysts CuBr and Li2CuCl4 and more efficient in the transference of secondary and tertiary alkyl groups than lower order cuprates (Gilman reagents) and demonstrated more reactivity than the lower order cuprates with its ability to couple primary Grignard reagents to secondary sulfonates. The Grignard reagent/catalyst system was compatible with an ester functionalized tosylate, thus proving to be more chemoselective than a Grignard reagent without the catalyst. The catalyst exhibited good reactivity below room temperature, and with the addition of 6% v/v of HMPA to the catalyst solution, excellent yields of coupled product were obtained within a 25-67°C temperature range. 1H NMR demonstrated that the catalyst solution consisted of several species that most likely were composed of copper ligated with thiophenol, THF, and LiBr in aggregated forms.
Geminal dialkylation, alkylative reduction and olefination of aliphatic aldehydes. Reaction of gem-bistriflates with higher order dialkylcyanocuprates
Garcia Martinez,Osio Barcina,Ruiz Diez,Subramanian
, p. 13231 - 13238 (2007/10/02)
gem-Dialkylation or alkylative reduction of α-unbranched aliphatic aldehydes 1 is advantageously achieved by reaction of the corresponding gem-bistriflates 2 with di-n-alkylcyanocuprates or di-sec- and di-tert-alkylcyanocuprates respectively. The reaction of α-branched gem-bistriflates 2 with dialkylcyanocuprates in the presence of boron trifluoride affords the olefins 6 in good yield.
Geminal Dialkylation and Alkylative Reduction of Alyphatic Aldehydes.
Martinez, A. Garcia,Fernandez, A. Herrera,Alvarez, R. Martinez,Barcina, J. Osio,Gomez, C. Garcia,Subramanian, L. R.
, p. 1063 - 1064 (2007/10/02)
gem-Dialkylation or alkylative reduction of α-unbranched aliphatic aldehydes is easily carried out by replacing the carbonyl oxygen with the gem-dihalide functionality followed by substitution of each halogen (bromine or iodine) by two n-alkyl groups or one sec- or tert-alkyl group and one hydrogen atom using higher-order dialkyl-lithium cyanocuprates.
