121611-57-2

Upstream product

• 108530-08-1 quinolin-8-yl trifluoromethanesulfonate 
• 66680-87-3 (2-phenylvinyl)tributylstannane 
• 100-42-5 styrene 
• 1613-37-2 Quinoline N-oxide 
• 132401-59-3 trans-8-styrylquinoline 
• 96911-08-9 8-ethenylquinoline 
• 100-58-3 phenylmagnesium bromide 

Downstream Products

• 132401-59-3 trans-8-styrylquinoline 
• 218-19-9 naphtho[1,2-h]quinoline 

Relevant academic research and scientific papers

Rh/O2-Catalyzed C8 Olefination of Quinoline N-Oxides with Activated and Unactivated Olefins

The rhodium/O2 system-catalyzed distal C(sp2)-H olefination of quinoline N-oxides is developed. Molecular oxygen has been explored as an economic and clean oxidant, an alternative to inorganic oxidants. A wide substrate scope with respect to quinoline N-oxides and olefins (activated acrylates and styrenes; unactivated aliphatic olefins) demonstrates the robustness of the developed catalytic method. Interestingly, 2-substituted quinoline N-oxides also afforded good yields of the corresponding C8-olefinated products. Kinetic isotope studies and deuterium-labeling experiments have been performed to understand the preliminary mechanistic pathway. The applicability of the developed method is demonstrated by utilizing natural product-derived substrates and by converting the C8-olefinated quinoline N-oxides into various other useful molecules.

Rhodium-Catalyzed Remote C-8 Alkylation of Quinolines with Activated and Unactivated Olefins: Mechanistic Study and Total Synthesis of EP4 Agonist

Reported herein is a rhodium(III)-catalyzed regioselective distal C(sp2)-H bond alkylation of quinoline N-oxides using olefins as alkyl source and N-oxide as the traceless directing group. The reaction exhibits broad substrate scope with excellent selectivity for C-8 position and good yields of alkylated products. The usefulness of the developed catalytic protocol is established by synthesis of EP4 agonist. In mechanistic study, C-8 olefinated quinoline was identified as the reaction intermediate, which gets reduced to desired C-8 alkylated product in the presence of a rhodium(I) species (produced from rhodium(III) during reaction) and formic acid. Formic acid is produced from dimethylformamide in the presence of silver tetrafluoroborate. (Figure presented.).

Adiabatic trans-cis photoisomerization and photocyclization of 8-styrylquinoline

Kinetics of the photocyclization of trans-8-styrylquinoline into 10a,10b-dihydronaphtho[1,2-h]quinoline (4-azachrysene) was studied in hexane. It was found that in addition to the expected two-step (two-quantum) route with trans-cis photoisomerization occurring in the first step with a quantum yield of Φtc = 0.13 with consequent photocyclization of the cis-isomer with a quantum yield of 0.23. The direct singlequantum photocyclization of the trans-isomer with a quantum yield of 0.009 is also observed. The latter observation indicates that the excited trans-isomer isomerizes without loss of excitation to the excited cis-isomer, which then undergoes cyclization, i.e., the trans-cis photoisomerization proceeds partially by adiabatic mechanism t* → c*.

Iron-catalyzed, directed oxidative arylation of olefins with organozinc and grignard reagents

(Figure presented) Chelation-controlled arylation of olefins with organozinc or Grignard reagents proceeds in the presence of an iron catalyst, under mild conditions and typically without the need of external ligands, to afford substituted olefins in high

Palladium-Mediated Transformations of Heteroaromatic Triflates

Quinolyl triflates and isoquinolyl triflates undergo palladium-catalysed couplings with organostannanes, organoaluminiums and activated alkenes.The range of organic groups which can be transferred to the heteroaromatic substrate includes aryl, vinyl, alkynyl, alkyl and hydride.