Pd-Catalyzed Chemodivergent Synthesis of 1-Indanones via Diethyl Zinc-Mediated Precise Switching of Umpolung Reactivity

Herein, we unveiled an efficient intramolecular umpolungchemodivergentcascade route for synthesizing 1-indanones via precisely switchingthe umpolung reactivity between the & alpha;-diketone and & pi;-allylPd complex. This successful merging of chemodivergent and umpolungstrategies is accomplished by employing a Pd catalyst and Et2Zn, which provides a broad array of 1-indanones with good yield andselectivity. The salient feature involves the amphiphilic behaviorsof both & alpha;-diketone and allyl functionality in two engineeredmild reaction conditions. Furthermore, scale up synthesis and postsynthetictransformations amplify the significance of the current protocol.Additionally, we have achieved the diastereomers of both ether andalcohol derivatives of 1-indanone efficiently via synthetic transformation.

Automated summary

Here, we have developed an efficient intramolecular umpolung chemodivergent cascade route for synthesizing 1-indanones by precisely controlling the umpolung reactivity between the α-diketone and π-allyl Pd complex. This strategy combines the advantages of chemodivergent and umpolung strategies, resulting in a broad array of 1-indanones with high yield and selectivity. The significance of this protocol is further amplified by the successful scale-up synthesis and post-synthetic transformations. Additionally, we have efficiently achieved diastereomers of ether and alcohol derivatives of 1-indanone through synthetic transformations.