4356-69-8Relevant academic research and scientific papers
Photoinduced Hydroarylation and Cyclization of Alkenes with Luminescent Platinum(II) Complexes
Cheng, Hanchao,Lam, Tsz-Lung,Liu, Yungen,Tang, Zhou,Che, Chi-Ming
supporting information, p. 1383 - 1389 (2020/11/30)
Photoinduced hydroarylation of alkenes is an appealing synthetic strategy for arene functionalization. Herein, we demonstrated that aryl radicals generated from electron-deficient aryl chlorides/bromides could be trapped by an array of terminal/internal aryl alkenes in the presence of [Pt(O^N^C^N)] under visible-light (410 nm) irradiation, affording anti-Markovnikov hydroarylated compounds in up to 95 % yield. Besides, a protocol for [Pt(O^N^C^N)]-catalyzed intramolecular photocyclization of acrylanilides to give structurally diverse 3,4-dihydroquinolinones has been developed.
Direct Allylic C(sp3)?H and Vinylic C(sp2)?H Thiolation with Hydrogen Evolution by Quantum Dots and Visible Light
Huang, Cheng,Ci, Rui-Nan,Qiao, Jia,Wang, Xu-Zhe,Feng, Ke,Chen, Bin,Tung, Chen-Ho,Wu, Li-Zhu
supporting information, p. 11779 - 11783 (2021/04/21)
Direct allylic C?H thiolation is straightforward for allylic C(sp3)?S bond formation. However, strong interactions between thiol and transition metal catalysts lead to deactivation of the catalytic cycle or oxidation of sulfur atom under oxidative condition. Thus, direct allylic C(sp3)?H thiolation has proved difficult. Represented herein is an exceptional for direct, efficient, atom- and step-economic thiolation of allylic C(sp3)?H and thiol S?H under visible light irradiation. Radical trapping experiments and electron paramagnetic resonance (EPR) spectroscopy identified the allylic radical and thiyl radical generated on the surface of photocatalyst quantum dots (QDs). The C?S bond formation does not require external oxidants and radical initiators, and hydrogen (H2) is produced as byproduct. When vinylic C(sp2)?H was used instead of allylic C(sp3)?H bond, the radical-radical cross-coupling of C(sp2)?H and S?H was achieved with liberation of H2. Such a unique transformation opens up a door toward direct C?H and S?H coupling for valuable organosulfur chemistry.
TMSOTf-mediated synthesis of skipped dienes through the addition of olefins to imines and semicyclicN,O-acetals
Feng, Yi-Man,Nie, Xiao-Di,Sun, Jian-Ting,Wei, Bang-Guo,Xu, Wen-Ke
, p. 7883 - 7893 (2021/09/28)
A novel approach to skipped dienes has been developed through the TMSOTf-mediated one-pot addition-substitution of olefins2a,2fand2gwith imines1a-1g, and a series of aryl substituted skipped dienes3aa-3gfwere accordingly obtained in 62%-94% yields. Moreov
Fritsch-Buttenberg-Wiechell rearrangement of magnesium alkylidene carbenoids leading to the formation of alkynes
Ando, Akane,Imafuji, Aki,Kimura, Tsutomu,Sekiguchi, Koto
, p. 1352 - 1359 (2021/06/06)
A series of 1-heteroatom-substituted vinyl p-tolyl sulfoxides were prepared and treated with organometallic reagents to evaluate which combination of sulfoxides and organometallic reagents yielded alkynes the most efficiently. The use of 1-chlorovinyl p-tolyl sulfoxide and isopropylmagnesium chloride was optimal for this purpose. A variety of 1-chlorovinyl p-tolyl sulfoxides were prepared from carbonyl compounds and chloromethyl p-tolyl sulfoxide and were converted into alkynes via the sulfoxide/magnesium exchange reaction and subsequent Fritsch-Buttenberg-Wiechell (FBW) rearrangement of the resulting magnesium alkylidene carbenoids. The mechanism of the FBW rearrangement of magnesium alkylidene carbenoids was studied by using13C-labeled sulfoxides and by using DFT calculations.
Deaminative carbonylative coupling of alkylamines with styrenes under transition-metal-free conditions
Zhao, Fengqian,Li, Chong-Liang,Wu, Xiao-Feng
supporting information, p. 9182 - 9185 (2020/08/26)
A transition-metal-free deaminative carbonylation of alkylamines with styrenes has been developed. The reaction shows good functional group compatibility and various α,β-unsaturated ketones were obtained in moderate to good yields. The alkyl radical generated from Katritzky salts via base-promoted C-N bond cleavage is one of the key intermediates in this reaction. This journal is
Base-promoted addition of DMA with 1,1-diarylethylenes: Application to a total synthesis of (-)-sacidumlignan B
Luo, Zhen-Biao,Peng, Yu,Wang, Ya-Wen
supporting information, p. 2054 - 2057 (2020/03/27)
A base-promoted addition of DMA (N,N-dimethylacetamide) to 1,1-diarylethylenes has been developed, and it provides a new strategy for the synthesis of N,N-dimethyl-4,4-diarylbutanamides from 1,1-diarylethylenes at room temperature. This method allows us to achieve the goal of synthesizing (-)-sacidumlignan B, and provides simple operation and broad substrate scope by avoiding the use of transition metal catalysts.
Synthesis of non-nucleoside anti-viral cyclopropylcarboxacyl hydrazones and initial anti-HSV-1 structure-activity relationship studies
Babu Dokuburra, Chanti,D'Aiuto, Leonardo,Demers, Matthew,McClain, Lora,McNulty, James,Nimgaonkar, Vishwajit L.,Piazza, Paolo,Williamson, Kelly,Zheng, Wenxiao
supporting information, (2020/10/02)
The synthesis of a lead anti-viral cyclopropyl carboxy acyl hydrazone 4F17 (5) and three sequential arrays of structural analogues along with the initial assessment and optimization of the antiviral pharmacophore against the herpes simplex virus type 1 (HSV-1) are reported.
Radical Aza-Cyclization of α-Imino-oxy Acids for Synthesis of Alkene-Containing N-Heterocycles via Dual Cobaloxime and Photoredox Catalysis
Tu, Jia-Lin,Liu, Jia-Li,Tang, Wan,Su, Ma,Liu, Feng
supporting information, p. 1222 - 1226 (2020/02/15)
Nitrogen-containing heterocycles are prevalent in both naturally and synthetically bioactive molecules. We report herein an unprecedented protocol for radical aza-cyclization of α-imino-oxy acids with pendant alkenes via synergistic photoredox and cobaloxime catalysis. With or without alkenes as the intermolecular cross-coupling partners, the transformation provides a variety of corresponding alkene-containing dihydropyrrole products in satisfactory yields. In the presence of external alkenes, the tandem reaction generates E-selective coupling products with excellent chemo- and stereoselectivity.
Enantioselective Radical-Polar Crossover Reactions of Indanonecarboxamides with Alkenes
Cao, Weidi,Feng, Xiaoming,Liu, Xiaohua,Wu, Wangbin,Xu, Xi,Yu, Han,Zhang, Xiying
supporting information, p. 4846 - 4850 (2020/02/11)
Highly efficient asymmetric intermolecular radical-polar crossover reactions were realized by combining a chiral N,N′-dioxide/NiII complex catalyst with Ag2O under mild reaction conditions. Various terminal alkenes and indanonecarboxamides/esters underwent radical addition/cyclization reactions to afford spiro-iminolactones and spirolactones with good to excellent yields (up to 99 %) and enantioselectivities (up to 97 % ee). Furthermore, a range of different radical-mediated oxidation/elimination or epoxide ring-opening products were obtained under mild reaction conditions. The Lewis acid catalysts exhibited excellent performance and precluded the strong background reaction.
Synthesis of N-Heterocycles by Reductive Cyclization of Nitroalkenes Using Molybdenum Hexacarbonyl as Carbon Monoxide Surrogate
Su, Zhiyou,Liu, Bo,Liao, Hongze,Lin, Hou-Wen
supporting information, p. 4059 - 4066 (2020/06/21)
The development of a method that uses molybdenum hexacarbonyl [Mo(CO)6] as carbon monoxide (CO) surrogate for the palladium-catalyzed reductive cyclization of nitroalkenes into indoles or thienopyrroles is reported. Several types of nitroalkenes could be transformed into the desired products in excellent yields and in most cases with complete regioselectivities and higher yields than those previously reported with palladium/CO system.
