2021
DOI: 10.1002/chem.202100043
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Palladium‐Catalyzed Difunctionalization of 1,3‐Diene with Amine and Disilane under a Mild Re‐oxidation System

Abstract: A highly regioselective and stereoselective difunctionalization reaction of 1,3‐diene with amine and disilane to form C−N and C−Si bonds via a one‐step Pd/Cu/O2 system is disclosed. The difunctionalization reaction affords allylic silanes, including the allylic amine moiety, in up to 92 % yield in the absence of any acid, base, or external ligand. The developed synthetic methodology can be scaled to 100 g in high yield with high Z‐selectivity, which demonstrates the feasibility of the reaction for industrial a… Show more

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Cited by 8 publications
(12 citation statements)
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“…Scheme 17 Oxidative silylation of 1-decene (12) with hexamethyldisilane (61) in the presence of Pd(OCOCF3) combined with acacH.…”
Section: Oxidative Silylation Of Terminal Alkenesmentioning
confidence: 99%
See 1 more Smart Citation
“…Scheme 17 Oxidative silylation of 1-decene (12) with hexamethyldisilane (61) in the presence of Pd(OCOCF3) combined with acacH.…”
Section: Oxidative Silylation Of Terminal Alkenesmentioning
confidence: 99%
“…Scheme 20 Pd-catalyzed difunctionalization of 2,3-dimethyl-1,3-butadiene (67) with N-methylaniline (66) and hexamethyldisilane (61).…”
Section: Oxidative Difunctionalization Of 13-dienesmentioning
confidence: 99%
“…[94] The effect of the solvent was attributed to a coordination phenomenon based on computational analysis. [95] Our group developed the Pd-catalyzed difunctionalization of 1,3-dienes with amines and disilanes to install nitrogen and silicon atoms at the allylic positions on hydrocarbons in a onestep process (Scheme 28). [96] The optimized conditions provided the product in an excellent yield (87 %) with high stereoselectivity (92 : 8, Z : E isomer ratio).…”
Section: Pd-catalyzed Aerobic Oxidative Multiple Formationmentioning
confidence: 99%
“…In a similar fashion, the solvent‐controlled Pd‐catalyzed aerobic 1,2‐aminooxygenation and 1,2‐oxyamination of conjugated dienes with 2‐aminophenols was also developed to form 1,4‐benzoxazines with highly chemoselectivity [94] . The effect of the solvent was attributed to a coordination phenomenon based on computational analysis [95] …”
Section: Synergic Pd‐catalyzed Aerobic Oxidative Coupling With Other ...mentioning
confidence: 99%
“…Several inter- and intramolecular oxidative coupling reactions using unsaturated compounds to form C–C or C–(heteroatom) bonds have been reported. Our group has also described methods for introducing an amino group to an olefin or 1,3-diene through an oxidative coupling mechanism . Although many groups have investigated oxidative amination reactions to form C–N bonds, studies involving oxidative alkoxylation reactions to form C–O bonds are rare.…”
mentioning
confidence: 99%