A diversity-oriented synthesis of bioactive benzanilides via a regioselective C(sp(2))-H hydroxylation strategy.

A diversity-oriented synthesis of bioactive benzanilides via a regioselective C(sp(2))-H hydroxylation strategy.
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通过区域选择性 C(sp2)–H 羟基化策略以多样性为导向合成生物活性苯甲酰苯胺

DOI:
10.1039/c5sc03905c
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发表时间:
2016-03-01
期刊:
影响因子:
8.4
通讯作者:
Rao Y
Rao Y
中科院分区:
化学1区
文献类型:
--
作者:
Sun YH;Sun TY;Wu YD;Zhang X;Rao Y

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研究了C(sp2)-H羟基化反应合成具有生物活性的苯甲酰苯胺类化合物。该反应表现出优异的区域选择性、良好的官能团耐受性和高产率。研究了C(sp2)-H羟基化反应合成具有生物活性的苯甲酰苯胺类化合物。不同的区域选择性,观察与Ru(ii)和Pd(ii)催化剂。该反应表现出优异的区域选择性、良好的官能团耐受性和高产率。通过这种新的合成策略,可以很容易地合成各种邻羟基苯甲酰苯胺,具有良好的区域选择性。计算研究表明,区域选择性主要受空间和电子因素的控制。空间效应决定了Ru催化反应的区域选择性结果,而电子效应在Pd催化反应中占主导地位。
A diversity-oriented synthesis of bioactive benzanilides via C(sp2)–H hydroxylation has been studied. The reaction demonstrates excellent regioselectivity, good tolerance of functional groups, and high yields. A diversity-oriented synthesis of bioactive benzanilides via C(sp2)–H hydroxylation has been studied. Different regioselectivity was observed with Ru(ii) and Pd(ii) catalysts. The reaction demonstrates excellent regioselectivity, good tolerance of functional groups, and high yields. A wide range of ortho-hydroxylated-benzanilides can be readily synthesized with excellent regioselectivity via this new synthetic strategy. Computational investigations revealed that the regioselectivity was controlled mainly by both steric and electronic factors. Steric effects determine the regioselective outcomes in the Ru-catalyzed reaction, while electronic effects are dominant in the Pd-catalyzed reaction.
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