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金催化的顺式二炔环化反应:金-芳炔相互作用本质的深入研究。

Gold-catalyzed cyclizations of cis-enediynes: insights into the nature of gold-aryne interactions.

机构信息

Department of Chemistry and Biochemistry, University of California, Santa Barbara, CA, USA.

出版信息

Angew Chem Int Ed Engl. 2013 Jul 22;52(30):7795-9. doi: 10.1002/anie.201301057. Epub 2013 Jun 20.

DOI:10.1002/anie.201301057
PMID:23788447
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC4120750/
Abstract

Golden aryne? Gold aryne complexes are inferred as transition states in dual gold-catalyzed cyclizations of cis-enediynes (see scheme; DCE = 1,2-dichloroethane). They are better described as ortho-aurophenyl cations, which react with weak nucleophiles and undergo facile intramolecular insertions into C(sp(3))-H bonds. Indanes, fused heteroarenes, and phenol derivatives are readily prepared using this method.

摘要

金炔烃?金炔烃配合物被推断为顺式二炔(见方案;DCE=1,2-二氯乙烷)双金催化环化反应的过渡态。它们更适合被描述为邻-金芳基阳离子,与弱亲核试剂反应,并容易发生分子内插入到 C(sp(3))-H 键中。使用这种方法可以很容易地制备茚、稠合杂环芳烃和苯酚衍生物。

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1
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2
Mechanistic switch in dual gold catalysis of diynes: C(sp(3))-H activation through bifurcation--vinylidene versus carbene pathways.炔烃的双金催化中的机理转换:C(sp(3))-H 活化的分叉——亚乙烯基与卡宾途径。
Angew Chem Int Ed Engl. 2013 Feb 25;52(9):2593-8. doi: 10.1002/anie.201208777. Epub 2013 Jan 30.
3
The hexadehydro-Diels-Alder reaction.六氢-Diels-Alder 反应。
Insights into Synergistic Effects of Counterion and Ligand on Diastereoselectivity Switch in Gold-Catalyzed Post-Ugi Ipso-Cyclization.
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ACS Omega. 2023 Jun 15;8(25):22637-22645. doi: 10.1021/acsomega.3c01279. eCollection 2023 Jun 27.
4
Gold-Catalyzed Annulation of 1,8-Dialkynylnaphthalenes: Synthesis and Photoelectric Properties of Indenophenalene-Based Derivatives.金催化的1,8-二炔基萘的环化反应:茚并菲衍生物的合成及光电性质
Chemistry. 2021 Feb 15;27(10):3552-3559. doi: 10.1002/chem.202004846. Epub 2021 Jan 19.
5
Synthesis of Fulvene Vinyl Ethers by Gold Catalysis.金催化合成富烯基乙烯基醚
Chemistry. 2020 Apr 21;26(23):5280-5287. doi: 10.1002/chem.202000338. Epub 2020 Apr 6.
6
Role of σ,π-Digold(I) Alkyne Complexes in Reactions of Enynes.σ,π-二金(I)炔配合物在烯炔反应中的作用
Organometallics. 2018 Mar 12;37(5):781-786. doi: 10.1021/acs.organomet.7b00668. Epub 2017 Dec 19.
7
Cryptic post-transition state bifurcations that reduce the efficiency of lactone-forming Rh-carbenoid C-H insertions.隐秘的过渡态后分叉降低了内酯形成的铑卡宾C-H插入反应的效率。
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A Switchable Gold Catalyst by Encapsulation in a Self-Assembled Cage.一种通过封装在自组装笼中实现的可切换金催化剂。
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J Am Chem Soc. 2012 Oct 24;134(42):17412-5. doi: 10.1021/ja307948m. Epub 2012 Oct 11.
5
Gold vinylidene complexes: intermolecular C(sp3)-H insertions and cyclopropanations pathways.金亚乙烯基配合物:分子间的 C(sp3)-H 插入和环丙烷化途径。
Angew Chem Int Ed Engl. 2012 Oct 15;51(42):10633-7. doi: 10.1002/anie.201204015. Epub 2012 Sep 17.
6
Gold-Catalyzed Regioselective Dimerization of Aliphatic Terminal Alkynes.金催化脂肪族末端炔烃的区域选择性二聚反应
Synlett. 2012 Jan;2012(1):54-56. doi: 10.1055/s-0031-1289567.
7
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Angew Chem Int Ed Engl. 2012 Aug 13;51(33):8156-9. doi: 10.1002/anie.201203587. Epub 2012 Jul 18.
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Gold(I)-catalyzed regioselective inter-/intramolecular addition cascade of di- and triynes for direct construction of substituted naphthalenes.金(I)催化的二炔和三炔的区域选择性的分子内/间加成级联反应,用于直接构建取代的萘。
J Org Chem. 2012 Jun 1;77(11):4907-16. doi: 10.1021/jo300771f. Epub 2012 May 15.
9
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10
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