54051-40-0Relevant articles and documents
Radical-Enabled Bicyclization Cascades of Oxygen-Tethered 1,7-Enynes Leading to Skeletally Diverse Polycyclic Chromen-2-ones
Jiang, Bo,Li, Jie,Pan, Yuanyuan,Hao, Wenjuan,Li, Guigen,Tu, Shujiang
, p. 323 - 334 (2017)
Catalytic bicyclization cascades of oxygen-tethered 1,7-enynes with simple cycloalkanes or aryl sulfonhydrazides have been established via subsequent multiple C-C bond-forming events from alkynyl/alkenyl functions, delivering a series of densely functiona
Synthesis of 3-alkyl spiro[4,5]trienones by copper-catalyzed oxidative ipso-annulation of activated alkynes with unactivated alkanes
Ouyang, Xuan-Hui,Song, Ren-Jie,Liu, Bang,Li, Jin-Heng
, p. 2573 - 2576 (2016)
A Cu-catalyzed oxidative ipso-annulation of activated alkynes with unactivated alkanes for the synthesis of 3-alkyl spiro[4,5]trienones is described. This method allows the formation of two carbon-carbon bonds and one carbon-oxygen bond in a single reaction through a sequence of C-H oxidative coupling, ipso-carbocyclization and dearomatization.
Visible-Light-Driven Palladium-Catalyzed Oxy-Alkylation of 2-(1-Arylvinyl)anilines by Unactivated Alkyl Bromides and CO2: Multicomponent Reactions toward 1,4-Dihydro-2 H-3,1-benzoxazin-2-ones
Sun, Song,Zhou, Cong,Yu, Jin-Tao,Cheng, Jiang
, p. 6579 - 6583 (2019)
A visible-light-driven palladium-catalyzed radical oxy-alkylation of 2-(1-arylvinyl)anilines with unactivated alkyl bromides and CO2 has been developed toward 1,4-dihydro-2H-3,1-benzoxazin-2-ones. This multicomponent reaction (MCR) starts with
Stereoselective C(sp2)-H Alkylation of Enamides with Unactivated Aliphatic Carboxylic Acids via Decarboxylative Cross-Coupling Reactions
Guo, Jing-Yu,Guan, Ting,Tao, Ji-Yu,Zhao, Kai,Loh, Teck-Peng
, p. 8395 - 8399 (2019)
An efficient and straightforward stereoselective alkylation reaction of enamides using commercially available and easily accessible unactivated alkyl carboxylic acids as alkylating agents is described, giving rise to a diverse array of synthetically impor
Metal-free tandem oxidative C(sp3)-H bond functionalization of alkanes and dearomatization of N-phenyl-cinnamamides: Access to alkylated 1-azaspiro[4.5]decanes
Zhang, Honglin,Gu, Zhangxi,Xu, Pan,Hu, Hongwen,Cheng, Yixiang,Zhu, Chengjian
, p. 477 - 480 (2016)
The TBPB promoted tandem oxidative C(sp3)-H bond functionalization of simple alkanes/alkylation-initiated dearomatization of N-phenyl-cinnamamides is reported, providing a direct method for the synthesis of alkylated 1-azaspiro[4.5]decanes with
Cascade alkylarylation of substituted N-allylbenzamides for the construction of dihydroisoquinolin-1(2H)-ones and isoquinoline-1,3(2H,4H)-diones
Qian, Ping,Du, Bingnan,Jiao, Wei,Mei, Haibo,Han, Jianlin,Pan, Yi
, p. 301 - 308 (2016)
An oxidative reaction for the synthesis of 4-alkyl-substituted dihydroisoquinolin-1(2H)-ones with N-allylbenzamide derivatives as starting materials has been developed. The radical alkylarylation reaction proceeds through a sequence of alkylation and intr
Copper-catalyzed thiocarbonylation and thiolation of alkyl iodides
Tian, Qingqiang,Sun, Rongjing,Li, Yahui
supporting information, p. 1186 - 1190 (2022/02/19)
In the present study, an efficient Cu-catalyzed transthiolation of alkyl iodides is developed. Notably, in the presence of CO, thioesters could also be obtained with copper and cobalt as the co-catalyst. This transformation displayed good functional group
A Metal-Free, Photocatalytic Method for Aerobic Alkane Iodination
Anna, Jessica M.,Goldberg, Karen I.,Hirscher, Nathanael A.,Ohri, Nidhi,Schelter, Eric J.,Yang, Qiaomu,Zhou, Jiawang
supporting information, p. 19262 - 19267 (2021/11/30)
Halogenation is an important alkane functionalization strategy, but O2 is widely considered the most desirable terminal oxidant. Here, the aerobic iodination of alkanes, including methane, was performed using catalytic [nBu4N]Cl and light irradiation (390 nm). Up to 10 turnovers of CH3I were obtained from CH4 and air, using a stop-flow microtubing system. Mechanistic studies using cyclohexane as the substrate revealed important details about the iodination reaction. Iodine (I2) serves multiple roles in the catalysis: (1) as the alkyl radical trap, (2) as a precursor for the light absorber, and (3) as a mediator of aerobic oxidation. The alkane activation is attributed to Cl? derived from photofragmentation of the electron donor-acceptor complex of I2 and Cl-. The kinetic profile of cyclohexane iodination showed that aerobic oxidation of I3- to produce I2 in CH3CN is turnover-limiting.
A general N-alkylation platform via copper metallaphotoredox and silyl radical activation of alkyl halides
Cabré, Albert,Dow, Nathan W.,MacMillan, David W. C.
supporting information, p. 1827 - 1842 (2021/07/07)
The catalytic union of amides, sulfonamides, anilines, imines, or N-heterocycles with a broad spectrum of electronically and sterically diverse alkyl bromides has been achieved via a visible-light-induced metallaphotoredox platform. The use of a halogen abstraction-radical capture (HARC) mechanism allows for room temperature coupling of C(sp3)-bromides using simple Cu(II) salts, effectively bypassing the prohibitively high barriers typically associated with thermally induced SN2 or SN1 N-alkylation. This regio- and chemoselective protocol is compatible with >10 classes of medicinally relevant N-nucleophiles, including established pharmaceutical agents, in addition to structurally diverse primary, secondary, and tertiary alkyl bromides. Furthermore, the capacity of HARC methodologies to engage conventionally inert coupling partners is highlighted via the union of N-nucleophiles with cyclopropyl bromides and unactivated alkyl chlorides, substrates that are incompatible with nucleophilic substitution pathways. Preliminary mechanistic experiments validate the dual catalytic, open-shell nature of this platform, which enables reactivity previously unattainable in traditional halide-based N-alkylation systems.
