钯催化碳-碳双键与双亲性有机（拟）卤化物的（杂）环化反应的最新进展
Recent advances in palladium-catalyzed (hetero)annulation of C[double bond, length as m-dash]C bonds with ambiphilic organo(pseudo)halides.
作者信息
Ni Hui-Qi, Cooper Phillippa, Engle Keary M
机构信息
The Scripps Research Institute, Department of Chemistry, 10550 N. Torrey Pines Rd, La Jolla, California, USA.
出版信息
Chem Commun (Camb). 2021 Aug 3;57(62):7610-7624. doi: 10.1039/d1cc02836g.
Abstract
Palladium has proven to be effective in catalyzing the (hetero)annulation of C[double bond, length as m-dash]C bonds with ambiphilic organo(pseudo)halides. Through the employment of appropriate ambiphilic coupling partners, efficient annulation of a variety of allenes, 1,3-dienes, strained alkenes, styrenes, and other C[double bond, length as m-dash]C bond variants can be achieved to provide direct access to numerous useful hetero- and carbocyclic scaffolds. In this Feature Article, we summarize palladium-catalyzed (hetero)annulation methods reported since 2005 (spanning just over 15 years) and discuss outstanding challenges in this area of study.
摘要
事实证明，钯在催化碳-碳双键与双亲性有机（拟）卤化物的（杂）环化反应中是有效的。通过使用合适的双亲性偶联试剂，可以实现各种丙二烯、1,3-二烯、张力烯烃、苯乙烯以及其他碳-碳双键变体的高效环化反应，从而直接构建出众多有用的杂环和碳环骨架。在这篇专题文章中，我们总结了自2005年以来（跨度超过15年）报道的钯催化（杂）环化方法，并讨论了该研究领域中存在的突出挑战。
相似文献
1
Recent advances in palladium-catalyzed (hetero)annulation of C[double bond, length as m-dash]C bonds with ambiphilic organo(pseudo)halides.钯催化碳-碳双键与双亲性有机（拟）卤化物的（杂）环化反应的最新进展
Chem Commun (Camb). 2021 Aug 3;57(62):7610-7624. doi: 10.1039/d1cc02836g.
2
Radical-mediated oxidative annulations of 1,n-enynes involving C-H functionalization.自由基促进的 1,n-烯炔的氧化环化反应：涉及 C-H 官能化。
Chem Commun (Camb). 2020 Jun 25;56(51):6907-6924. doi: 10.1039/d0cc02335c.
3
C[double bond, length as m-dash]N bond formation via palladium-catalyzed carbene insertion into N[double bond, length as m-dash]N bonds: inhibiting the general 1,2-migration process of ylide intermediates.通过钯催化卡宾插入N=N键形成C=N键：抑制叶立德中间体的一般1,2-迁移过程。
Chem Commun (Camb). 2017 Feb 28;53(18):2697-2700. doi: 10.1039/c6cc10187a.
4
Catalytic σ-Bond Annulation with Ambiphilic Organohalides Enabled by β-X Elimination.通过β-X消除实现的与双亲性有机卤化物的催化σ键环化反应
Angew Chem Int Ed Engl. 2023 Aug 21;62(34):e202306581. doi: 10.1002/anie.202306581. Epub 2023 Jul 13.
5
The selective activation of a C-F bond with an auxiliary strong Lewis acid: a method to change the activation preference of C-F and C-H bonds.利用辅助强路易斯酸对碳-氟键进行选择性活化：一种改变碳-氟键和碳-氢键活化偏好的方法。
Dalton Trans. 2016 Nov 15;45(45):18133-18141. doi: 10.1039/c6dt03235d.
6
Mapping Ambiphile Reactivity Trends in the Anti-(Hetero)annulation of Non-Conjugated Alkenes via Pd /Pd Catalysis.通过 Pd/Pd 催化对非共轭烯烃的反-（杂）环加成反应中双亲试剂反应性趋势的映射。
Angew Chem Int Ed Engl. 2022 Mar 21;61(13):e202114346. doi: 10.1002/anie.202114346. Epub 2022 Feb 2.
7
Copper(I)-catalyzed carbon-halogen bond-selective boryl substitution of alkyl halides bearing terminal alkene moieties.铜（I）催化的带有末端烯烃部分的卤代烷烃的碳-卤键选择性硼基取代反应。
Chem Commun (Camb). 2015 Jun 14;51(47):9655-8. doi: 10.1039/c5cc02760h.
8
[3+2]-Annulation of platinum-bound azomethine ylides with distal C[double bond, length as m-dash]C bonds of N-allenamides.铂键合的甲亚胺叶立德与N-烯丙酰胺远端C═C键的[3 + 2]环化反应
Chem Commun (Camb). 2016 Dec 20;53(1):196-199. doi: 10.1039/c6cc07874e.
9
Cu-catalyzed oxygenation of alkene-tethered amides with O unactivated C[double bond, length as m-dash]C bond cleavage: a direct approach to cyclic imides.铜催化烯基连接酰胺的氧化反应，通过未活化的碳-碳双键断裂实现：一种合成环状酰亚胺的直接方法。
Chem Sci. 2019 Aug 6;10(39):9099-9103. doi: 10.1039/c9sc03175h. eCollection 2019 Oct 21.
10
The mechanism and origin of the regioselectivity of cobalt-catalyzed annulation of allenes with benzamide: a computational study.钴催化丙二烯与苯甲酰胺环化反应区域选择性的机制和起源：计算研究。
Dalton Trans. 2018 Oct 2;47(38):13592-13601. doi: 10.1039/c8dt02476f.
引用本文的文献
1
Enantioselective Heck/Tsuji-Trost reaction of flexible vinylic halides with 1,3-dienes.柔性乙烯基卤化物与1,3-二烯的对映选择性Heck/Tsuji-Trost反应。
Nat Commun. 2025 Jan 22;16(1):930. doi: 10.1038/s41467-025-56142-z.
2
Ligand control of regioselectivity in palladium-catalyzed heteroannulation reactions of 1,3-Dienes.配体对钯催化1,3 - 二烯杂环化反应区域选择性的控制
Nat Commun. 2024 Jun 26;15(1):5433. doi: 10.1038/s41467-024-49803-y.
3
Dienes as Versatile Substrates for Transition Metal-Catalyzed Reactions.二烯作为过渡金属催化反应的通用底物
Angew Chem Int Ed Engl. 2024 May 13;63(20):e202401550. doi: 10.1002/anie.202401550. Epub 2024 Mar 19.
4
Construction of azaheterocycles via Pd-catalyzed migratory cycloannulation reaction of unactivated alkenes.钯催化的非活化烯烃的迁移环化反应构建氮杂杂环。
Nat Commun. 2022 Aug 27;13(1):5059. doi: 10.1038/s41467-022-32726-x.
5
Convergent Synthesis of Dihydrobenzofurans via Urea Ligand-Enabled Heteroannulation of 2-Bromophenols with 1,3-Dienes.脲配体促进的 2-溴苯酚与 1,3-二烯的杂环化反应制备二氢苯并呋喃
Org Lett. 2022 Aug 12;24(31):5787-5790. doi: 10.1021/acs.orglett.2c02301. Epub 2022 Jul 29.
6
Mapping Ambiphile Reactivity Trends in the Anti-(Hetero)annulation of Non-Conjugated Alkenes via Pd /Pd Catalysis.通过 Pd/Pd 催化对非共轭烯烃的反-（杂）环加成反应中双亲试剂反应性趋势的映射。
Angew Chem Int Ed Engl. 2022 Mar 21;61(13):e202114346. doi: 10.1002/anie.202114346. Epub 2022 Feb 2.
本文引用的文献
1
Kinetic Resolution of Allyltriflamides through a Pd-Catalyzed C-H Functionalization with Allenes: Asymmetric Assembly of Tetrahydropyridines.通过钯催化的烯丙基三氟酰胺与丙二烯的 C-H 功能化实现动力学拆分：四氢吡啶的不对称组装。
J Am Chem Soc. 2021 Mar 17;143(10):3747-3752. doi: 10.1021/jacs.1c01929. Epub 2021 Mar 2.
2
Anti-selective [3+2] (Hetero)annulation of non-conjugated alkenes via directed nucleopalladation.非共轭烯烃的定向氮钯化[3+2]（杂）环化反应。
Nat Commun. 2020 Dec 22;11(1):6432. doi: 10.1038/s41467-020-20182-4.
3
Pd/Xiang-Phos-catalyzed enantioselective intermolecular carboheterofunctionalization of norbornene and norbornadiene.钯/相转移催化剂促进的降冰片烯和降冰片二烯的对映选择性分子间碳杂官能化反应。
Chem Commun (Camb). 2020 Nov 7;56(86):13125-13128. doi: 10.1039/d0cc04996d. Epub 2020 Oct 2.
4
Pd/Xiang-Phos-catalyzed enantioselective intermolecular carboheterofunctionalization under mild conditions.钯/湘磷催化的温和条件下对映选择性分子间碳杂官能化反应
Chem Sci. 2020 May 29;11(24):6283-6288. doi: 10.1039/d0sc01391a. eCollection 2020 Jun 28.
5
Chelating Group Enabled Palladium-Catalyzed Regiodivergent Carbonylative Synthesis of 2,3-Dihydroquinolin-4(1H)-ones.螯合基团促进的钯催化区域发散羰基化合成 2,3-二氢喹啉-4(1H)-酮。
Chemistry. 2020 Nov 17;26(64):14565-14569. doi: 10.1002/chem.202003003. Epub 2020 Oct 14.
6
Palladium-Catalyzed [5 + 2] Heteroannulation of Phenethylamides with 1,3-Dienes to Dopaminergic 3-Benzazepines.钯催化苯乙酰胺与 1,3-二烯的[5 + 2]杂环加成反应构建多巴胺能 3-苯并氮杂卓。
Org Lett. 2020 May 1;22(9):3591-3595. doi: 10.1021/acs.orglett.0c01053. Epub 2020 Apr 19.
7
Synthesis and antiproliferative activity of 6-naphthylpterocarpans.6-萘基蝶啶类化合物的合成及抗增殖活性。
Org Biomol Chem. 2020 Mar 18;18(11):2148-2162. doi: 10.1039/d0ob00110d.
8
α-Halogenoacetamides: versatile and efficient tools for the synthesis of complex aza-heterocycles.α-卤代乙酰胺：合成复杂氮杂环的多功能、高效工具。
Org Biomol Chem. 2019 Sep 25;17(37):8467-8485. doi: 10.1039/c9ob01683j.
9
Pd/PC-Phos-Catalyzed Enantioselective Intermolecular Denitrogenative Cyclization of Benzotriazoles with Allenes and N-Allenamides.钯/手性磷酸协同催化苯并三唑与烯丙基化合物和 N-烯丙酰胺的对映选择性分子间 denitrogenative 环化反应。
Angew Chem Int Ed Engl. 2019 Aug 12;58(33):11444-11448. doi: 10.1002/anie.201904805. Epub 2019 Jul 4.
10
Pd(II)-Catalyzed Asymmetric Oxidative Annulation of N-Alkoxyheteroaryl Amides and 1,3-Dienes.钯（II）催化的N-烷氧基杂芳基酰胺与1,3-二烯的不对称氧化环化反应
Org Lett. 2019 Apr 5;21(7):2048-2051. doi: 10.1021/acs.orglett.9b00216. Epub 2019 Mar 22.
Zotero 插件