1160063-34-2Relevant academic research and scientific papers
Rhodium(II)-Catalyzed and Thermally Induced Intramolecular Migration of N-Sulfonyl-1,2,3-triazoles: New Approaches to 1,2-Dihydroisoquinolines and 1-Indanones
Sun, Run,Jiang, Yu,Tang, Xiang-Ying,Shi, Min
, p. 5727 - 5733 (2016/04/20)
New rhodium(II)-catalyzed or thermally induced intramolecular alkoxy group migration of N-sulfonyl-1,2,3-triazoles has been developed, affording divergent synthesis of 1,2-dihydroisoquinoline and 1-indanone derivatives according to different conditions. N-Sulfonyl keteneimine is the key intermediate for the synthesis of dihydroisoquinoline, whereas the aza-vinyl carbene intermediate results in the formation of 1-indanone.
Intramolecular C-H activation through gold(I)-catalyzed reaction of iodoalkynes
Morn-Poladura, Pablo,Rubio, Eduardo,Gonzlez, Jos M.
, p. 3052 - 3055 (2015/04/14)
The cycloisomerization reaction of 1-(iodoethynyl)-2-(1-methoxyalkyl)arenes and related 2-alkyl-substituted derivatives gives the corresponding 3-iodo-1-substituted-1H-indene under the catalytic influence of IPrAuNTf2 [IPr = 1,3-bis(2,6-diisopropyl)phenylimidazol-2-ylidene; NTf2 = bis(trifluoromethanesulfonyl)imidate]. The reaction takes place in 1,2-dichloroethane at 80°C, and the addition of ttbp (2,4,6-tritert-butylpyrimidine) is beneficial to accomplish this new transformation in high yield. The overall reaction implies initial assembly of an intermediate gold vinylidene upon alkyne activation by gold(I) and a 1,2-iodine-shift. Deuterium labeling and crossover experiments, the magnitude of the recorded kinetic primary isotopic effect, and the results obtained from the reaction of selected stereochemical probes strongly provide support for concerted insertion of the benzylic C-H bond into gold vinylidene as the step responsible for the formation of the new carbon-carbon bond.
Platinum and ruthenium chloride-catalyzed cycloisomerization of 1-alkyl-2-ethynylbenzenes: Interception of π-activated alkynes with a benzylic C-H bond
Tobisu, Mamoru,Nakai, Hiromi,Chatani, Naoto
supporting information; experimental part, p. 5471 - 5475 (2009/12/06)
(Chemical Equation Presented) Air-stable and commercially available alkynophilicmetal salts, such as PtCl2, PtCl4, and [RuCl2(CO)3]2, catalyze the cycloisomerization of 1-alkyl-2-ethynylbenzenes to produce substituted indenes even at an ambient temperature. Electrophilically activated alkynes can be intercepted by simple benzylic C-Hbonds at primary, secondary, and tertiary carbon centers. Mechanistic studies, such as labeling studies and kinetic isotope and substituent effects, indicate that the cycloisomerization proceeds through the formation of a vinylidene intermediate and turnover-limiting 1,5-shift of benzylic hydrogen.
