2021
DOI: 10.1002/chem.202005443
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Abstract: Transition metal-catalyzed [4+ +2+ +1] reactions of dienes (or diene derivatives such as vinylallenes), alkynes/ alkenes, and CO (or carbenes)a re expected to be the most straightforward approacht os ynthesize challenging seven-membered ring compounds, but so far only limited successes have been realized. Here, an unexpected threecomponent [4+ +2+ +1] reactionb etweent wo vinylallenes and CO was discovered to give highlyf unctionalized tropone derivatives under mild conditions, where one vinylallene acts as aC… Show more

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Cited by 5 publications
(4 citation statements)
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“…This agrees with experiments of Wender et al 3a First, we discuss Figure 4b for the substrate with a common diene. Consistent with the previous studies on the reductive elimination from the d 6 In Figure 4a for the substrate with a CP-capped diene, all the [2 + 2 + 1] pathways have similar activation free energies compared to those in Figure 4b for the substrate with a common diene: 25.9 kcal/mol (TS5-CO) vs 24.3 kcal/mol (TS5-CO-d); 33.3 kcal/mol (TS5) vs 33.2 kcal/mol (TS5-d). However, the [4 + 2 + 1] pathways for the substrate with a CPcapped diene compared to those for the substrate with a common diene are favored by around 7 kcal/mol: 20.1 kcal/ mol (TS4) vs 27.1 kcal/mol (TS4-d); 24.0 kcal/mol (TS4-CO) vs 32.1 kcal/mol (TS4-CO-d).…”
Section: ■ Introductionsupporting
confidence: 93%
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“…This agrees with experiments of Wender et al 3a First, we discuss Figure 4b for the substrate with a common diene. Consistent with the previous studies on the reductive elimination from the d 6 In Figure 4a for the substrate with a CP-capped diene, all the [2 + 2 + 1] pathways have similar activation free energies compared to those in Figure 4b for the substrate with a common diene: 25.9 kcal/mol (TS5-CO) vs 24.3 kcal/mol (TS5-CO-d); 33.3 kcal/mol (TS5) vs 33.2 kcal/mol (TS5-d). However, the [4 + 2 + 1] pathways for the substrate with a CPcapped diene compared to those for the substrate with a common diene are favored by around 7 kcal/mol: 20.1 kcal/ mol (TS4) vs 27.1 kcal/mol (TS4-d); 24.0 kcal/mol (TS4-CO) vs 32.1 kcal/mol (TS4-CO-d).…”
Section: ■ Introductionsupporting
confidence: 93%
“…In our opinion, one of the most efficient and straightforward reactions, needed to be developed for the synthesis of seven-membered carbocycles, is the transition-metal-catalyzed [4 + 2 + 1] cycloaddition of diene-enes/diene-ynes/diene-allenes and carbon monoxide (CO), considering that these substrates are readily accessible and CO is cheap and abundant. However, realization of this reaction has obstacles, since [4 + 2], [2 + 2 + 1] cycloadditions and other side reactions could overwhelm the desired [4 + 2 + 1] cycloaddition.…”
Section: Introductionmentioning
confidence: 99%
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“…Fortunately, our group discovered a rhodium-catalyzed [4 + 2 + 1] cycloaddition of in situ generated ene/yne–ene–allenes from ene/yne–ene propargyl esters with CO, which can be regarded as a [4 + 2 + 1] cycloaddition using the SDS strategy (Schemes c and ). This new [4 + 2 + 1] reaction is efficient to get access to 5/7 fused rings, and several selected examples are given in Scheme a. Therefore, it is crucial to understand how this [4 + 2 + 1] cycloaddition takes place.…”
Section: Introductionmentioning
confidence: 99%