Journal
CHEMICAL RECORD
Volume 21, Issue 12, Pages 3483-3497Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/tcr.202100099
Keywords
boranes; stannanes; copper; palladium; Lewis acidity
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Funding
- JSPS KAKENHI [JP16H01031, JP17K05864]
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In this study, a B(dan) moiety of diminished boron-Lewis acidity was efficiently installed into organic frameworks through copper catalyzed three-component carboboration of alkenes. The resulting dan-substituted organoboranes were obtained via borylative substitution of carbon electrophiles. Additionally, synthesis of diverse organostannanes based upon copper-catalyzed carbostannylation and borylstannylation have been described, where the Lewis acidity increment of a tin center facilitated the progress in some cases.
A B(dan) moiety (dan=naphthalene-1,8-diaminato) of diminished boron-Lewis acidity has efficiently been installed into organic frameworks by three-component carboboration of alkenes under copper catalysis, where a Cu-B(dan) species, generated by chemoselective sigma-bond metathesis between a copper catalyst and an unsymmetrical diboron [(pin)B-B(dan)], acts as a key intermediate. The Cu-B(dan) species has also turned out to serve as a B(dan) nucleophile to afford various dan-substituted organoboranes via borylative substitution of carbon electrophiles. Furthermore, borylation reactions with another Lewis acidity-diminished boron unit, B(aam) (aam=anthranilamidato), have become feasible by use of (pin)B-B(aam) or H-B(aam). The resulting dan/aam-substituted organoboranes have been demonstrated to undergo direct cross-coupling without prior acidic deprotection, regardless of their diminished boron-Lewis acidity. Synthesis of diverse organostannanes based upon copper-catalyzed carbostannylation and borylstannylation, in which Lewis acidity increment of a tin center facilitates the progress in some cases, have also been described.
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