Zinc-Mediated Decarboxylative Alkylation of Gem-difluoroalkenes DOI

Liting Yu,

Mei‐Lin Tang, Chang‐Mei Si

et al.

Organic Letters, Journal Year: 2018, Volume and Issue: 20(15), P. 4579 - 4583

Published: July 19, 2018

An efficient and mild zinc-mediated decarboxylative alkylation of gem-difluoroalkenes with N-hydroxyphthalimide (NHP) esters, to give monofluoroalkenes in moderate excellent yields high Z-selectivity is reported. The reaction tolerates a broad range functional groups can be easily scaled up, which thus may pave the way for its further applications medicinal chemistry materials science.

Language: Английский

Palladium-catalyzed regioselective C–H fluoroalkylation of indoles at the C4-position DOI

Arun Jyoti Borah,

Zhuangzhi Shi

Chemical Communications, Journal Year: 2017, Volume and Issue: 53(28), P. 3945 - 3948

Published: Jan. 1, 2017

An exclusive catalytic C4-selective fluoroalkylation of indoles with highly active (1H, 1H-perfluoroalkyl)mesityliodonium triflate has been described.

Language: Английский

Citations

102

Direct Access to Cobaltacycles via C–H Activation: N-Chloroamide-Enabled Room-Temperature Synthesis of Heterocycles DOI
Xiaolong Yu,

Kehao Chen,

Shan Guo

et al.

Organic Letters, Journal Year: 2017, Volume and Issue: 19(19), P. 5348 - 5351

Published: Sept. 19, 2017

Cobaltacycle synthesis via C-H activation has been achieved for the first time, providing key mechanistic insight into cobalt catalytic chemistry. N-Chloroamides are used as a directing synthon cobalt-catalyzed room-temperature and construction of heterocycles. Alkynes coupling partners allow convenient access to isoquinolones, class synthetically pharmaceutically important compounds. The broad substrate scope enables diverse range substitution patterns be incorporated heterocyclic scaffold.

Language: Английский

Citations

98

Synthesis of Alkylated Monofluoroalkenes via Fe-Catalyzed Defluorinative Cross-Coupling of Donor Alkenes with gem-Difluoroalkenes DOI
Ling Yang, Weiwei Ji, E. Lin

et al.

Organic Letters, Journal Year: 2018, Volume and Issue: 20(7), P. 1924 - 1927

Published: March 19, 2018

A reductive cross-coupling of gem-difluoroalkenes with diverse unactivated and heteroatom substituted olefins through a Fe-catalyzed hydrogen atom transfer (HAT) strategy is reported. Different from the previous HAT-type olefin reactions, presence fluorine in molecule results stereoselective β-F cleavage, leading to C(sp2)–C(sp3) bond formation. wide variety alkylated monofluoroalkenes were obtained good efficiency excellent Z selectivity under air- water-tolerant reaction conditions. similar defluorinative coupling was also realized.

Language: Английский

Citations

98

Rh(III)-Catalyzed and Solvent-Controlled Chemoselective Synthesis of Chalcone and Benzofuran Frameworks via Synergistic Dual Directing Groups Enabled Regioselective C–H Functionalization: A Combined Experimental and Computational Study DOI
Wei Yi, Weijie Chen,

Fu‐Xiaomin Liu

et al.

ACS Catalysis, Journal Year: 2018, Volume and Issue: 8(10), P. 9508 - 9519

Published: Sept. 5, 2018

By virtue of a synergistically dual-directing-group (the O–NHAc part and the hydroxyl group)-assisted strategy, efficient practical Rh(III)-catalyzed regioselective redox-neutral C–H functionalization diverse N-phenoxyacetamides with propargyl alcohols has been realized, which led to divergent synthesis privileged benzofuran chalcone frameworks in solvent-controlled chemoselective manner. Experimental computational studies reveal that formation hydrogen bonding between dual directing groups subsequent coordination interaction group Rh(III) catalyst play decisive role promoting migratory insertion alkyne moiety. Thereafter, two switchable reaction pathways, respectively involve tandem β–H elimination/hydrogen transfer/oxidative addition/C–O bond reductive elimination/oxidation (for low-polar solvents: path I–Ia via RhIII–RhI–RhIII pathway) oxidative addition/β–H transfer/protonolysis high-polar II–IIb RhIII–RhV–RhIII pathway), are followed deliver corresponding products excellent chemoselectivity. Taken together, our results presented here not only give an expansion area O–NHAc-directed activations but also provide rational basis for future development synergistic DGs-enabled reactions.

Language: Английский

Citations

87

Zinc-Mediated Decarboxylative Alkylation of Gem-difluoroalkenes DOI

Liting Yu,

Mei‐Lin Tang, Chang‐Mei Si

et al.

Organic Letters, Journal Year: 2018, Volume and Issue: 20(15), P. 4579 - 4583

Published: July 19, 2018

An efficient and mild zinc-mediated decarboxylative alkylation of gem-difluoroalkenes with N-hydroxyphthalimide (NHP) esters, to give monofluoroalkenes in moderate excellent yields high Z-selectivity is reported. The reaction tolerates a broad range functional groups can be easily scaled up, which thus may pave the way for its further applications medicinal chemistry materials science.

Language: Английский

Citations

85