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Synthesis of 7,7′-Dihydroxy-8,8′-biquinolyl (azaBINOL) via Pd-Catalyzed Directed Double C–H Functionalization of 8,8′-Biquinolyl: Emergence of an Atropos from a Tropos State

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Figshare2016-02-23 更新2026-04-29 收录
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https://figshare.com/articles/dataset/Synthesis_of_7_7_Dihydroxy_8_8_biquinolyl_azaBINOL_via_Pd_Catalyzed_Directed_Double_C_H_Functionalization_of_8_8_Biquinolyl_Emergence_of_an_i_Atropos_i_from_a_i_Tropos_i_State/2625822
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7,7′-Dihydroxy-8,8′-biquinolyl (azaBINOL) was prepared from 2-chloroaniline in four steps: (1) the Skraup reaction, (2) Ni-catalyzed reductive coupling of 8-chloroquinoline, (3) Pd(II)-catalyzed double C–H functionalization of 8,8′-biquinolyl mediated by PhI(OAc)2, and (4) saponification. During the third step, an axially chiral (atropos type) biaryl molecule was directly generated from an essentially achiral (tropos type) biaryl starting material.
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2016-02-23
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