2883-12-7Relevant academic research and scientific papers
Iron-Based Catalyst for Borylation of Unactivated Alkyl Halides without Using Highly Basic Organometallic Reagents
Siddiqui, Sheema,Bhawar, Ramesh,Geetharani
, p. 1948 - 1954 (2021/01/14)
The mild borylation of alkyl bromides and chlorides with bis(neopentylglycolato)diborane (B2neop2) mediated by iron-bis amide is described. The reaction proceeds with a broad substrate scope and good functional group compatibility. Moreover, sufficient ca
Copper-catalyzed reduction of alkyl triflates and iodides: An efficient method for the deoxygenation of primary and secondary alcohols
Dang, Hester,Cox, Nick,Lalic, Gojko
, p. 752 - 756 (2014/01/23)
We describe an effective method for catalytic reduction of 1°alkyl sulfonates, and 1°and 2°iodides in the presence of a wide range of functional groups. This Cu-catalyzed reaction provides a means for the effective deoxygenation of alcohols, as demonstrated by the highly selective reduction of 1°alcohols using a triflation/reduction sequence. A preliminary study of the reaction mechanism suggests that the reduction does not involve free-radical intermediates. Primarily reduced: The copper-catalyzed reduction of 1°alkyl sulfonates, and 1°and 2°iodides, which is effective in the presence of a wide range of functional groups, provides a means for the effective deoxygenation of alcohols. A preliminary study of the reaction mechanism suggests that the reduction does not involve free-radical intermediates. Copyright
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.
NHC-copper hydrides as chemoselective reducing agents: Catalytic reduction of alkynes, alkyl triflates, and alkyl halides
Cox, Nick,Dang, Hester,Whittaker, Aaron M.,Lalic, Gojko
, p. 4219 - 4231 (2014/06/09)
The NHC-copper-catalyzed Z-selective semi-reduction of terminal and internal alkynes, as well as the NHC-copper-catalyzed reduction of primary alkyl triflates and primary and secondary alkyl iodides and bromides are described. The high chemoselectivity demonstrated in these examples illustrates the mild nature of copper hydride complexes as reducing agents, which have applications in synthetic chemistry beyond their traditional role in the reduction of activated alkenes and carbonyl compounds.
Silver-catalyzed cross-coupling reactions of alkyl bromides with alkyl or aryl Grignard reagents
Someya, Hidenori,Yorimitsu, Hideki,Oshima, Koichiro
supporting information; experimental part, p. 3270 - 3272 (2009/08/09)
Treatment of secondary or tertiary alkyl bromides with alkyl Grignard reagents in the presence of catalytic amounts of silver bromide and potassium fluoride in CH2Cl2 afforded the corresponding cross-coupling products in reasonable yields. Moreover, silver showed catalytic activity for the cross-coupling reactions of alkyl bromides with aryl Grignard reagents.
Alkyl-alkyl Suzuki cross-couplings of unactivated secondary alkyl halides at room temperature
Saito, Bunnai,Fu, Gregory C.
, p. 9602 - 9603 (2008/02/12)
A commercially available 1,2-diamine serves as an effective ligand for metal-catalyzed cross-couplings of unactivated alkyl electrophiles at room temperature. In particular, Ni/trans-N,N′-dimethyl-1,2-cyclohexanediamine provides the first method for achie
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.
