2020
DOI: 10.1021/acscatal.0c01596
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Development of Ketone-Based Brominating Agents (KBA) for the Practical Asymmetric α-Bromination of Aldehydes Catalyzed by Tritylpyrrolidine

Abstract: Ketone-based brominating agents (KBA), orthosubstituted 2,2,2-tribromoacetophenones, have been developed, and the highly enantioselective and practical α-bromination of aldehydes with KBA was achieved. The reaction could be performed in the presence of only 0.1−1 mol % of catalyst without using a halogenated solvent at 0 °C and was found to be scalable.

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Cited by 17 publications
(24 citation statements)
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“…Bromination follows the same trend as the other halogenation reactions, in that due to the hazardous nature of elemental bromine, which is a strong irritant, a few practical reagents have been developed as bromine transfer agents that are popular in the laboratory (Figure 62). New ones continue to be developed [146,147] . Nevertheless, in many applications bromine is still used.…”
Section: Brominationmentioning
confidence: 99%
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“…Bromination follows the same trend as the other halogenation reactions, in that due to the hazardous nature of elemental bromine, which is a strong irritant, a few practical reagents have been developed as bromine transfer agents that are popular in the laboratory (Figure 62). New ones continue to be developed [146,147] . Nevertheless, in many applications bromine is still used.…”
Section: Brominationmentioning
confidence: 99%
“…New ones continue to be developed. [146,147] Nevertheless, in many applications bromine is still used.…”
Section: Brominationmentioning
confidence: 99%
“… 4 7 These α-bromination reactions provide highly versatile chiral building blocks that can be rapidly derivatized to α-bromoimines, 8a azidoalcohols, 8b epoxides, 8c or bromohydrins ( Figure 1 ). 4 7 …”
Section: Introductionmentioning
confidence: 99%
“…In 2020, Maruoka and Kano explored alternative aminocatalytic methods using pyrrolidine derivatives instead of 3c as catalyst ( Figure 2 d). 7 They reported the rapid decomposition of NBS ( 2a ) and 4,4-dibromo-2,6-di- tert -butyl-cyclohexa-2,5-dienone ( 2c ) in the presence of pyrrolidine and explored milder brominating agents to avoid the bromination of the pyrrolidine derivatives used as catalysts. They explored several noncommercially available ketone-based brominating agents (KBAs) and chose to use ClPh-KBA 2d ( Figure 2 d).…”
Section: Introductionmentioning
confidence: 99%
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