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2021
DOI: 10.31635/ccschem.020.202000579
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Copper-Catalyzed Carbonylative Synthesis of β-Boryl Amides via Boroamidation of Alkenes

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Cited by 33 publications
(22 citation statements)
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References 50 publications
(19 reference statements)
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“…Moreover, we further expanded the success of this synergetic catalysis system to the more challenging four-component reaction radical carbonylative carbocyanation. Notably, CO would coordinatively saturate the Cu center and/or compete with cyanides and chiral ligands, thus making the chiral Cu catalyst ineffective or making radical carbonylative carbocyanation unordered. To our delight, preliminary experiments indicated that the four-component reactions with 1,3-diene 1a or 1,3-enyne 8c occurred in an orderly manner, affording chiral allyl ketocyanide 10 and chiral propargyl ketocyanide 11 in moderate yields and high enantioselectivities (Figure b, 10 : 46% yield and 91% ee; 11 : 48% yield and 88% ee).…”
mentioning
confidence: 99%
“…Moreover, we further expanded the success of this synergetic catalysis system to the more challenging four-component reaction radical carbonylative carbocyanation. Notably, CO would coordinatively saturate the Cu center and/or compete with cyanides and chiral ligands, thus making the chiral Cu catalyst ineffective or making radical carbonylative carbocyanation unordered. To our delight, preliminary experiments indicated that the four-component reactions with 1,3-diene 1a or 1,3-enyne 8c occurred in an orderly manner, affording chiral allyl ketocyanide 10 and chiral propargyl ketocyanide 11 in moderate yields and high enantioselectivities (Figure b, 10 : 46% yield and 91% ee; 11 : 48% yield and 88% ee).…”
mentioning
confidence: 99%
“…A possible pathway was proposed based on previous studies 15,16,19 and the experimental results discussed above (Scheme 5). At first, bis(pinacolato)diboron (B 2 pin 2 ) transferred a boryl group to the copper center in the presence of base.…”
Section: Resultsmentioning
confidence: 99%
“…22,23 Likewise, Fe-bound acyl units can act as structural models of the Fe hydrogenase active site. 24 For copper, however, these unstable species have been proposed as intermediates in Cu-catalysed reactions such as borocarbonylation and amidation, 25 but have not been isolated, due to their propensity to undergo facile rearrangement.…”
mentioning
confidence: 99%