Divergent synthesis of 3,4-dihydrodibenzo[b,d]furan-1(2H)-ones and isocoumarins via additive-controlled chemoselective C-C or C-N bond cleavage

Zuo Youpeng; He Xinwei; Ning Yi; Zhang Lanlan; Wu Yuhao; Shang Yongjia

首页> 外文期刊>New Journal of Chemistry >Divergent synthesis of 3,4-dihydrodibenzo[b,d]furan-1(2H)-ones and isocoumarins via additive-controlled chemoselective C-C or C-N bond cleavage

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Divergent synthesis of 3,4-dihydrodibenzo[b,d]furan-1(2H)-ones and isocoumarins via additive-controlled chemoselective C-C or C-N bond cleavage

机译：通过添加控制的化学选择性C-C或C-N键裂解，发散合成3,4-二氢苯并二苯甲苯[B，D]呋喃-1（2H） - 酮和异壳素

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Rh(III)-Catalyzed C-C/C-O bond formation between cyclic 2-diazo-1,3-diketones and salicylamides with additive-controlled chemoselectivity is described. The reaction proceeded under mild reaction conditions and exhibited good functional group tolerance and scalability. 3,4-Dihydrodibenzo[b, d]furan-1(2H)-ones were obtained in moderate to excellent yields (55-90%) through a tandem N-H activation/C-C cleavage/etherification process when AgNTf2 was used as the additive, whereas utilizing Cu(OAc)(2) afforded isocoumarins in good yields (60-86%) via a C-H activation/C-N cleavage/lactonization pathway.

机译：[RH（III） - 描述了环状2-二氮杂-1,3-二酮与具有添加剂控制的化学选择性的水杨酸之间的催化C-C / C-O键形成。反应在温和的反应条件下进行，并表现出良好的官能团耐受性和可扩展性。当AgNTF2用作添加剂时，通过串联NH激活/ CC切割/醚化方法，获得3,4-二氢苯肼苯并[B，D]呋喃-1（2H）酮在中等至优异的产率（55-90％）。然而，利用Cu（OAC）（2）通过CH激活/ CN切割/内酰胺途径得到良好的产率（60-86％）提供的异壳。

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《New Journal of Chemistry》 |2018年第3期|共9页
作者
Zuo Youpeng; He Xinwei; Ning Yi; Zhang Lanlan; Wu Yuhao; Shang Yongjia;
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作者单位

Anhui Normal Univ Key Lab Funct Mol Solids Minist Educ Coll Chem &

Mat Sci Anhui Lab Mol Based Mat State Key Lab Cultivat Ba Wuhu 241000 Peoples R China;

Anhui Normal Univ Key Lab Funct Mol Solids Minist Educ Coll Chem &

Mat Sci Anhui Lab Mol Based Mat State Key Lab Cultivat Ba Wuhu 241000 Peoples R China;

Anhui Normal Univ Key Lab Funct Mol Solids Minist Educ Coll Chem &

Mat Sci Anhui Lab Mol Based Mat State Key Lab Cultivat Ba Wuhu 241000 Peoples R China;

Anhui Normal Univ Key Lab Funct Mol Solids Minist Educ Coll Chem &

Mat Sci Anhui Lab Mol Based Mat State Key Lab Cultivat Ba Wuhu 241000 Peoples R China;

Anhui Normal Univ Key Lab Funct Mol Solids Minist Educ Coll Chem &

Mat Sci Anhui Lab Mol Based Mat State Key Lab Cultivat Ba Wuhu 241000 Peoples R China;

Anhui Normal Univ Key Lab Funct Mol Solids Minist Educ Coll Chem &

Mat Sci Anhui Lab Mol Based Mat State Key Lab Cultivat Ba Wuhu 241000 Peoples R China;

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正文语种 eng
中图分类化学;
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1. Divergent synthesis of 3,4-dihydrodibenzo[b,d]furan-1(2H)-ones and isocoumarins via additive-controlled chemoselective C-C or C-N bond cleavage [J] . Zuo Youpeng, He Xinwei, Ning Yi, New Journal of Chemistry . 2018,第3期

机译：通过添加控制的化学选择性C-C或C-N键裂解，发散合成3,4-二氢苯并二苯甲苯[B，D]呋喃-1（2H） - 酮和异壳素
2. Cu-catalyzed reaction of 1,2-dihalobenzenes with 1,3-cyclohexanediones for the synthesis of 3,4-dihydrodibenzo[b,d]furan-1(2H)-ones [J] . Aljaar N., Malakar C.C., Conrad J., The Journal of Organic Chemistry . 2012,第18期

机译：铜催化1,2-二卤苯与1,3-环己二酮合成3,4-二氢二苯并[b，d]呋喃-1（2H）-ones
3. Copper-catalyzed and iodide-promoted aerobic C-C bond cleavage/C-N bond formation toward the synthesis of amides [J] . Wu Kun, Huang Zhiliang, Ma Yiyang, RSC Advances . 2016,第29期

机译：铜催化和碘化物促进的有氧C-C键切割/ C-N键形成酰胺的合成
4. C-N and C-C Bonds Cleavage of Substituted Pyridines by a Trinuclear Ti Hydride Complex [C] . Shaowei Hu, Takanori Shima, Zhaomin Hou 日本化学会春季年会講演予稿集 . 2018

机译：C-N和C-C键通过三核TI氢化物复合物切割取代吡啶
5. Catalytic C-C (C-N) Bond Formation and C-O Bond Cleavage by Pincer-Ligated Iridium Complexes [D] . Li, Bo. 2019

机译：掺杂剂铱络合物催化C-C（C-N）键合形成和C-O键切割
6. C-C bond cleavage in biosynthesis of 4-alkyl-L-proline precursors of lincomycin and anthramycin cannot precede C-methylation [O] . Zdenek Kamenik, Radek Gazak, Stanislav Kadlcik, -1

机译：林可霉素和蒽霉素的4-烷基-L-脯氨酸前体生物合成中的C-C键断裂不能先于C-甲基化
7. Reactions of a Ru(II) Phenyl Complex with Substrates that Possess C-N or C-O Multiple Bonds: C-C Bond Formation, N-H Bond Cleavage, and Decarbonylation Reactions [O] . Lee, John P., Pittard, Karl A., DeYonker, Nathan J., 2006

机译：Ru（II）苯基配合物与具有C-N或C-O多键的底物的反应：C-C键形成，N-H键断裂和脱羰反应

Divergent synthesis of 3,4-dihydrodibenzo[b,d]furan-1(2H)-ones and isocoumarins via additive-controlled chemoselective C-C or C-N bond cleavage

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