Fig. 9: Synthetic application. | Nature Communications

Fig. 9: Synthetic application.

From: Three-component diels-alder reaction through palladium carbene migratory insertion enabled dearomative C(sp3)-H bond activation

Fig. 9: Synthetic application.The alternative text for this image may have been generated using AI.

a Manipulation from 4a. b Manipulation from 6a. c Trapping the in situ generated o-QDM with trifluoroacetophone 16. Conditions and reagents: (i) 4a, NBS, DCM, 0 °C, 6 h. (ii) PhB(OH)2, Pd(PPh3)4, K2CO3, 1,4-dioxane:H2O = 4:1, 80 °C, 12 h. (iii) TFA, DCM, 50 °C, 2 h. (iv) ArB(OH)2, Pd(PPh3)4, K2CO3, 1,4-dioxane:H2O = 4:1, 80 °C, 12 h. (v) 6a, DDQ, DBU, DCM, RT, 6 h. (vi) 6a, Li/naphthalene, THF, 0 °C, 2 h. (vii) a 1a, 2a, 16, Pd(OAc)2 10 mol%, (4-MeC6H4)3P 15 mol%, K3PO4, THF, 80 °C, 12 h; b TsOH·H2O, DCM, RT, 6 h. Me: methyl, Ts: 4-methylbenzenesulfonyl, DDQ: 2,3-dichloro-5,6-dicyanobenzoquinone, RT: room temperature.

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