- Benzyne 1,2,4-Trisubstitution and Dearomative 1,2,4-Trifunctionalization
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Both 1,2,4-trisubstitution and dearomative 1,2,4-trifunctionalization of benzyne have been accomplished from sulfoxides bearing a penta-2,4-dien-1-yl moiety. These cascade transformations proceed through a benzyne insertion into the S═O bond and an uncommon regiospecific anionic [4,5]-sigmatropic rearrangement, furnishing a C-O, C-S, and C-C bond on the C1-, C2-, and C4-position of a benzene ring, respectively. This study showcases new cascade benzyne reaction modes involving both distal C-H bond functionalization and dearomatization.
- Chen, Zhonghong,Dai, Liang,Lan, Yu,Li, Lianggui,Li, Yang,Shan, Chunhui,Shi, Jiarong,Tan, Min
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supporting information
p. 10530 - 10536
(2021/07/28)
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- Selective: S -arylation of 2-oxazolidinethiones and selective N -arylation of 2-benzoxazolinones/2-benzimidazolinones
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There exist three possible patterns for the reaction of cyclic 2-oxazolidinethione and 2-benzoxazolidinethione with arynes, namely (a) S-arylation, (b) N-arylation, and (c) aryne insertion into the thiocarbonyl group (CS). Our studies demonstrate that S-arylation wins out affording S-aryl dihydrooxazoles. In contrast, for related reactions of cyclic 2-benzoxazolinone and 2-benzimidazolinone with arynes, it is found that N-arylation outcompetes O-arylation and aryne insertion into the CO group to give N-aryl 2-benzoxazolinones and N-aryl 2-benzimidazolinones.
- Sun, Chu-Han,Lu, Yi,Zhang, Qing,Lu, Rong,Bao, Lin-Qing,Shen, Mei-Hua,Xu, Hua-Dong
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p. 4058 - 4063
(2017/07/10)
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- An efficient procedure for the synthesis of ortho-trialkylsilylaryl triflates: Easy access to precursors of functionalized arynes
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o-Trialkylsilylaryl triflates which are useful aryne precursors are prepared from o-bromophenols by an efficient, one-pot procedure involving O-silylation, metal-halogen exchange, O- to C-silyl migration, and entrapment of the phenoxide with triflic anhydride.
- Pena, Diego,Cobas, Agustin,Perez, Dolores,Guitian, Enrique
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p. 1454 - 1458
(2007/10/03)
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