区域选择性
化学
醌
立体化学
催化作用
组合化学
有机化学
作者
Hongyin Gao,Qing‐Long Xu,Craig Keene,Muhammed Yousufuddin,Daniel H. Ess,László Kürti
标识
DOI:10.1002/anie.201508419
摘要
Abstract An organic acid catalyzed direct arylation of aromatic C(sp 2 )H bonds in phenols and naphthols for the preparation of 1,1′‐linked functionalized biaryls was developed. The products are non‐C 2 ‐symmetrical, atropoisomeric, and represent previously untapped chemical space. Overall this transformation is operationally simple, does not require an external oxidant, is readily scaled up (up to 98 mmol), and the structurally diverse 2,2′‐dihydroxy biaryl (i.e., BINOL‐type), as well as 2‐amino‐2′‐hydroxy products (i.e., NOBIN‐type) are formed with complete regioselectivity. Density‐functional calculations suggest that the quinone and imino‐quinone monoacetal coupling partners are exclusively arylated at their α‐position by an asynchronous [3,3]‐sigmatropic rearrangement of a mixed acetal species which is formed in situ under the reaction conditions.
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