A Novel Cascade Benzyne Nucleophilic Addition/Fries Rearrangement for Entry into 2,3-Disubstituted Phenols (vol 28, pg 799, 2017)

被引:0
作者
Bronner, Sarah M.
Lee, Daniel
Bacauanu, Vlad
Cyr, Patrick
机构
[1] Genentech Inc., 1 DNA Way, South San Francisco, 94080-4918, CA
关键词
aryne; benzyne; Fries rearrangement; reactive intermediate; silyltriflate;
D O I
10.1055/s-0036-1589495
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A cascade benzyne Fries rearrangement is reported that offers facile access to 2,3-disubstituted phenols, allowing for two points of diversity on the benzyne adduct. The methodology utilizes an o-(trimethylsilyl) triflate phenol as a common intermediate, from which substitution of the phenolic oxygen readily yields benzyne precursors that undergo the requisite rearrangement in the presence of an amine nucleophile, base, and a fluoride source.
引用
收藏
页码:E2 / E2
页数:1
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  • [1] Bronner SM, 2017, SYNLETT, V28, P799, DOI 10.1055/s-0036-1588938