Negishi Cross-Coupling Is Compatible with a Reactive B-Cl Bond: Development of a Versatile Late-Stage Functionalization of 1,2-Azaborines and Its Application to the Synthesis of New BN Isosteres of Naphthalene and Indenyl.
Negishi Cross-Coupling Is Compatible with a Reactive B-Cl Bond: Development of a Versatile Late-Stage Functionalization of 1,2-Azaborines and Its Application to the Synthesis of New BN Isosteres of Naphthalene and Indenyl.
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DOI：
10.1021/jacs.5b05879
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发表时间：
2015-07-22
影响因子：
15
通讯作者：
Liu SY
中科院分区：
文献类型：
--
作者：
Brown AN;Li B;Liu SY
Negishi 交叉偶联反应与多功能 B-Cl 官能团的兼容性已在 1,2-氮杂硼烷的后期官能化中得到证明。烷基、芳基和烯基锌试剂已用于三正交前体 3-溴-1-(叔丁基二甲基甲硅烷基)-2-氯-1,2-二氢-1,2-氮杂硼烷 (2) 的官能化，以提供新的 2,3-取代单环 1,2-氮杂硼烷。这种方法能够从常见的中间体合成以前难以捉摸的BN-萘和BN-茚基结构。
The compatibility of the Negishi cross-coupling reaction with the versatile B–Cl functionality has been demonstrated in the context of late-stage functionalization of 1,2-azaborines. Alkyl-, aryl-, and alkenylzinc reagents have been utilized for the functionalization of the triply orthogonal precursor 3-bromo-1-(tert-butyldimethylsilyl)-2-chloro-1,2-dihydro-1,2-azaborine (2) to furnish new 2,3-substituted monocyclic 1,2-azaborines. This methodology has enabled the synthesis of previously elusive BN-naphthalene and BN-indenyl structures from a common intermediate.