《Dearomative 1,4-difunctionalization of naphthalenes via palladium-catalyzed tandem Heck/Suzuki coupling reaction》 was published in Nature Communications in 2020. These research results belong to Zhou, Bo; Wang, Hongliang; Cao, Zhong-Yan; Zhu, Jia-Wen; Liang, Ren-Xiao; Hong, Xin; Jia, Yi-Xia. Application of 768-35-4 The article mentions the following:
Reported herein is an application of naphthalenes I [R = 2-bromophenyl, N-(2-bromophenyl)-N-methylcarbamoyl, 2-bromo-5-(methoxycarbonyl)phenoxymethyl, N-(3-bromopyridin-2-yl)-N-methylcarbamoyl, etc.; R1 = H, OMe; R2 = H, Br; R3 = H, OMe; R4 = H; R3R4 = -CH=CH-CH=CH-] as a masked conjugated diene in a palladium-catalyzed dearomative 1,4-diarylation or 1,4-vinylarylation reaction via tandem Heck/Suzuki sequence. Three types of 1,4-dihydronaphthalene-based spirocyclic compounds II [X = N, CH; R5 = Me, Bn; R6 = H, 4-F, 5-OMe, 6-CF3, etc.; R7 = Ph, 4-ethenylphenyl, 3,4-difluorophenyl, etc.; R8 = H, Ph]/III [R9 = H, 4-Me, 4-OMe, 4-F, 5-Me, 5-F; R10 = Et, n-Pr, Ph, etc.; R11 = Ph, 3-methylphenyl, naphthalen-2-yl] are achieved in excellent regio- and diastereoselectivities. Key to this transformation is the inhibition of a few competitive side reactions, including intramol. naphthalenyl C-H arylation, intermol. Suzuki cross-coupling, dearomative 1,2-difunctionalization, and dearomative reductive-Heck reaction. D. functional theory (DFT) calculations imply that the facile exergonic dearomative insertion of a naphthalene double bond disrupts the sequence of direct Suzuki coupling, leading to the tandem Heck/Suzuki coupling reaction. The observed regioselectivity towards 1,4-difunctionalization is due to the steric repulsions between the introduced aryl group and the spiro-scaffold in 1,2-difunctionalization. The experimental process involved the reaction of (3-Fluorophenyl)boronic acid(cas: 768-35-4Application of 768-35-4)
(3-Fluorophenyl)boronic acid(cas: 768-35-4) can be used to make novel liquid crystalline fluorobiphenylcyclohexenes and difluoroterphenyls by palladium-catalyzed cross-couplings also used in the synthesis of o-phenylphenols as potent leukotriene B4 receptor agonists.Application of 768-35-4
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