57647-92-4Relevant articles and documents
Coupling of Reformatsky Reagents with Aryl Chlorides Enabled by Ylide-Functionalized Phosphine Ligands
Hu, Zhiyong,Wei, Xiao-Jing,Handelmann, Jens,Seitz, Ann-Katrin,Rodstein, Ilja,Gessner, Viktoria H.,Goo?en, Lukas J.
supporting information, p. 6778 - 6783 (2021/02/01)
The coupling of aryl chlorides with Reformatsky reagents is a desirable strategy for the construction of α-aryl esters but has so far been substantially limited in the substrate scope due to many challenges posed by various possible side reactions. This limitation has now been overcome by the tailoring of ylide-functionalized phosphines to fit the requirements of Negishi couplings. Record-setting activities were achieved in palladium-catalyzed arylations of organozinc reagents with aryl electrophiles using a cyclohexyl-YPhos ligand bearing an ortho-tolyl-substituent in the backbone. This highly electron-rich, bulky ligand enables the use of aryl chlorides in room temperature couplings of Reformatsky reagents. The reaction scope covers diversely functionalized arylacetic and arylpropionic acid derivatives. Aryl bromides and chlorides can be converted selectively over triflate electrophiles, which permits consecutive coupling strategies.
Application of sulfuryl chloride for the quick construction of β-chlorotetrahydrofuran derivatives from homoallylic alcohols under mild conditions
Zeng, Xianghua,Miao, Chengxia,Wang, Shoufeng,Xia, Chungu,Sun, Wei
supporting information, p. 2391 - 2396 (2013/09/23)
An efficient and mild method is reported for the construction of β-chlorotetrahydrofuran derivatives by 5-endo chlorocycloetherification of homoallylic alcohols. The system employs sulfuryl chloride as the chlorinating agent under catalyst-free conditions. A variety of homoallylic alcohols with aryl or alkyl substituents were smoothly converted into β- chlorotetrahydrofurans in yields up to 98%.
Kinetics and regioselectivity of ring opening of 1-bicyclo[3.1.0] hexanylmethyl radical
Kantorowski, Eric J.,Le, Daniel D.,Hunt, Caleb J.,Barry-Holson, Keegan Q.,Lee, Jessica P.,Ross, Lauren N.
, p. 1593 - 1596 (2008/09/17)
(Chemical Equation Presented) Rate constants for the rearrangement of 1-bicyclo[3.1.0]-hexanylmethyl radical (2) to 3-methylenecyclohexenyl radical (3) and 2-methylenecyclopentyl-1-methyl radical (1) were measured using the PTOC-thiol competition method. The ring-expansion pathway is described by the rate equation, log(k/s-1) = (12.5 ± 0.1) - (4.9 ± 0.1)/θ; the non-expansion pathway is described by log(k/s-1) = (11.9 ± 0.6) - (6.9 ± 0.8)/θ. Employing the slower trapping agent, tri-n-butylstannane, favors methylenecyclohexane over 2-methyl-methylenecyclopentane by more than 120:1 at ambient or lower temperatures.
