2018
DOI: 10.1021/acscatal.8b03059
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CO2-Catalyzed Efficient Dehydrogenation of Amines with Detailed Mechanistic and Kinetic Studies

Abstract: Contents: 1. Materials and methods 2. General procedure for the oxidation of amines to imines 3. Setup for photocatalytic reactions 4. Optimization 5. Mechanistic experiments 6. Theoretical calculations 7. Characterization of products 8. References 9. NMR spectra Materials and methodsCommercial reagents were used without purification and reactions were run under CO2 atmosphere with exclusion of moisture from reagents using standard techniques for manipulating air-sensitive compounds. In case of dry DBN used fo… Show more

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Cited by 68 publications
(60 citation statements)
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“…Unexpectedly, conversion was observed under these conditions, albeit to a lesser extent: ∼38 % conversion under aerobic conditions (Table ). We hypothesized that the cosolvent, DMSO present in 5 % v/v may act as the oxidizing agent in the absence of dioxygen as observed by Das and coworkers . Substituting DMSO with DMF however, led to conversion both with and without dioxygen (Table S7).…”
Section: Methodsmentioning
confidence: 72%
“…Unexpectedly, conversion was observed under these conditions, albeit to a lesser extent: ∼38 % conversion under aerobic conditions (Table ). We hypothesized that the cosolvent, DMSO present in 5 % v/v may act as the oxidizing agent in the absence of dioxygen as observed by Das and coworkers . Substituting DMSO with DMF however, led to conversion both with and without dioxygen (Table S7).…”
Section: Methodsmentioning
confidence: 72%
“…Started from DBTO, in the absence of light (under air atmosphere, with PhIO as oxidant), only DBTO 2 from the oxidation of DBTO was formed in 89% yield ( Supplementary Table 1, entry 3), and lack of t-BuOOH and (or) catalyst led to reduce of DBTO to DBT (Supplementary Table 1, entries 4-6). The reaction was inhibited dramatically by radical quenchers such as (2,2,6,6-tetramethylpiperidin-1-yl)oxyl (TEMPO) and butylated hydroxytoluene (BHT) suggested a radical pathway (Supplementary Table 1, entries 7-10) [51][52][53] . Furthermore, addition of 1.0 equiv.…”
Section: -21 For Reaction Progress Monitored By Hplc)mentioning
confidence: 99%
“…Furthermore, addition of 1.0 equiv. of CuCl 2 to the reaction mixture resulted in the formation of BPS in 59% yield (HPLC yield) (Supplementary Table 1, entry 11), which revealed a singleelectron processes may be involved in this photochemical process [51][52][53] .…”
Section: -21 For Reaction Progress Monitored By Hplc)mentioning
confidence: 99%
“…More recently, Das group also demonstrated cyclization of the diamines 189 and aldehydes 190 into heterocycles 191 , but in different reaction conditions [83] (Scheme 27). Opposite to the previous example, this protocol is based on CO 2 -catalyzed dehydrogenation/aromatization of amines under photoredox conditions.…”
Section: Application Of Visible-light-mediated Catalysis In Synthementioning
confidence: 99%