- Catalyst-Free Visible-Light-Mediated Iodoamination of Olefins and Synthetic Applications
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Herein we report a catalyst- and metal-free visible-light-mediated protocol enabling the iodoamination of miscellaneous olefins. This protocol is characterized by high yields under environmentally benign reaction conditions utilizing commercially available substrates and a green and biodegradable solvent. Furthermore, the protocol allows for late-stage functionalization of bioactive molecules and can be scaled to gram quantities of product, which offers manifold possibilities for further transformations, including morpholine, piperidine, pyrrolidine, and aziridine synthesis.
- Engl, Sebastian,Reiser, Oliver
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supporting information
p. 5581 - 5586
(2021/07/26)
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- Decarboxylative Negishi Coupling of Redox-Active Aliphatic Esters by Cobalt Catalysis
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A cobalt-catalyzed decarboxylative Negishi coupling reaction of redox-active aliphatic esters with organozinc reagents was developed. The method enabled efficient alkyl–aryl, alkyl–alkenyl, and alkyl–alkynyl coupling reactions under mild reaction conditions with no external ligand or additive needed. The success of an in situ activation protocol and the facile synthesis of the drug molecule (±)-preclamol highlight the synthetic potential of this method. Mechanistic studies indicated that a radical mechanism is involved.
- Liu, Xu-Ge,Zhou, Chu-Jun,Lin,Han, Xiang-Lei,Zhang, Shang-Shi,Li, Qingjiang,Wang, Honggen
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supporting information
p. 13096 - 13100
(2018/09/21)
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- DIRECT ANTI-MARKOVNIKOV ADDITION OF ACIDS TO ALKENES
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A method of making an anti-Markovnikov addition product, comprises reacting an acid with an alkene or alkyne in a dual catalyst reaction system to the exclusion of oxygen to produce said anti-Markovnikov addition product; the dual catalyst reaction system comprising a single electron oxidation catalyst in combination with a hydrogen atom donor catalyst. Dual catalyst composition useful for carrying out such methods are also described.
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Paragraph 0104; 0105; 0123; 0124
(2016/05/02)
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- Anti-markovnikov hydroamination of alkenes catalyzed by an organic photoredox system
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Herein we report a metal-free method for the direct anti-Markovnikov hydroamination of unsaturated amines. Irradiation of the amine substrates with visible light in the presence of catalytic quantities of easily synthesized 9-mesityl-10-methylacridinium t
- Nguyen, Tien M.,Nicewicz, David A.
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supporting information
p. 9588 - 9591
(2013/07/26)
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- Highly flexible synthesis of chiral azacycles via iridium-catalyzed hydrogenation
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A range of saturated chiral azacycles has been prepared in high yield and with high selectivity from simple starting materials. A modular approach with ring-closing metathesis as a key step was used to produce a number of five-, six-, and seven-membered c
- Verendel, J. Johan,Zhou, Taigang,Li, Jia-Qi,Paptchikhine, Alexander,Lebedev, Oleg,Andersson, Pher G.
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supporting information; experimental part
p. 8880 - 8881
(2010/08/22)
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- Concise synthesis of 3-arylpiperidines
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We present an easy and straightforward synthesis of 3-arylpiperidines by Grignard addition of piperidin-3-one with different arylmagnesium bromide reagents and acidic dehydroxylation of the resulting tertiary alcohol with the combination of triethylsilane and boron trifluoride etherate. This facile strategy was further used to synthesize preclamol. A highly regioselective dehydration of 3-arylpiperidin-3-ol with boron trifluoride etherate was investigated for preparing 3-aryl-1,4,5,6-tetrahydropyridine skeleton. A novel selenium dioxide mediated dihydroperoxidation of 3-aryl-1,4,5,6-tetrahydropyridine was also examined.
- Chang, Meng-Yang,Hsu, Ru-Ting,Chen, Hua-Ping,Lin, Pei-Jung
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p. 1173 - 1183
(2007/10/03)
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