芳烃对苯酚进行芳基化反应的不同反应途径：并苯和2-芳基苯酚的合成
Divergent Reaction Pathways for Phenol Arylation by Arynes: Synthesis of Helicenes and 2-Arylphenols.
作者信息
Truong Thanh, Daugulis Olafs
机构信息
Department of Chemistry, University of Houston, Houston, TX 77204-5003, USA.
出版信息
Chem Sci. 2013;4:531-535. doi: 10.1039/c2sc21288a.
Abstract
Two reactions of phenols with arynes have been developed. If LiTMP base is employed, arynes generated from aryl chlorides react with phenols to form helicenes. -Arylation of phenols can be achieved by employing BuONa base in the presence of AgOAc. Direct arylation of binol was achieved leading to the shortest pathway to o,o'-diarylbinols.
摘要
已经开发出酚类与芳炔的两种反应。如果使用LiTMP碱，由芳基氯生成的芳炔与酚类反应形成螺旋烯。在醋酸银存在下使用丁醇钠碱可实现酚类的芳基化。实现了联萘酚的直接芳基化，从而得到了制备邻，邻'-二芳基联萘酚的最短途径。
相似文献
1
Divergent Reaction Pathways for Phenol Arylation by Arynes: Synthesis of Helicenes and 2-Arylphenols.芳烃对苯酚进行芳基化反应的不同反应途径：并苯和2-芳基苯酚的合成
Chem Sci. 2013;4:531-535. doi: 10.1039/c2sc21288a.
2
Employing Arynes in Diels-Alder Reactions and Transition-Metal-Free Multicomponent Coupling and Arylation Reactions.芳炔在 Diels-Alder 反应和过渡金属自由的多组分偶联和芳基化反应中的应用。
Acc Chem Res. 2016 Sep 20;49(9):1658-70. doi: 10.1021/acs.accounts.6b00188. Epub 2016 Aug 25.
3
Employing Arynes for the Generation of Aryl Anion Equivalents and Subsequent Reaction with Aldehydes.利用芳炔生成芳基阴离子等价物并随后与醛反应。
J Org Chem. 2018 Sep 21;83(18):11333-11340. doi: 10.1021/acs.joc.8b01549. Epub 2018 Jul 19.
4
Synthesis of aryl ethers of carbohydrates via reaction with arynes: selective O-arylation of trans-vicinal dihydroxyl groups in carbohydrates.通过与芳炔反应合成碳水化合物的芳基醚：碳水化合物中反式顺式二羟基的选择性 O-芳基化。
Org Biomol Chem. 2020 Jun 10;18(22):4174-4177. doi: 10.1039/d0ob00540a.
5
Selective S-arylation of 2-oxazolidinethiones and selective N-arylation of 2-benzoxazolinones/2-benzimidazolinones.2-恶唑烷硫酮的选择性S-芳基化及2-苯并恶唑啉酮/2-苯并咪唑啉酮的选择性N-芳基化。
Org Biomol Chem. 2017 May 16;15(19):4058-4063. doi: 10.1039/c7ob00040e.
6
(2-Pyridyl)acetone-promoted Cu-catalyzed O-arylation of phenols with aryl iodides, bromides, and chlorides.（2-吡啶基）丙酮促进的铜催化酚的 O-芳基化反应，所用芳基碘化物、溴化物和氯化物。
J Org Chem. 2009 Sep 18;74(18):7187-90. doi: 10.1021/jo9012157.
7
Decarbethoxylative Arylation Employing Arynes: A Metal-Free Pathway to Arylfluoroamides.脱羰芳基化反应：一种无需金属的芳基氟酰胺合成方法。
Org Lett. 2017 Nov 3;19(21):6016-6019. doi: 10.1021/acs.orglett.7b03072.
8
Palladium-Catalyzed Cascade Cyclization/Dearomatization/Arylation of Alkyne-Containing Phenol-Based Biaryls with Aryl Halides: An Entry to Diversely Functionalized Spirocyclohexadienones.钯催化的含炔基苯酚基联芳烃的级联环化/去芳构化/芳基化反应：一种用于合成多官能化螺环己二烯酮的方法。
J Org Chem. 2020 May 15;85(10):6687-6696. doi: 10.1021/acs.joc.0c00710. Epub 2020 May 7.
9
Catalytic direct arylation with aryl chlorides, bromides, and iodides: intramolecular studies leading to new intermolecular reactions.与芳基氯、溴和碘的催化直接芳基化：分子内研究引发新的分子间反应
J Am Chem Soc. 2006 Jan 18;128(2):581-90. doi: 10.1021/ja055819x.
10
Chemoselectivity in the Cu-catalyzed O-arylation of phenols and aliphatic alcohols.铜催化酚和脂肪醇的 O-芳基化反应中的化学选择性。
Chem Commun (Camb). 2011 Aug 7;47(29):8340-2. doi: 10.1039/c1cc12694f. Epub 2011 Jun 23.
引用本文的文献
1
Intermolecular Asymmetric Arylative Dearomatization of 1-Naphthols.1-萘酚的分子间不对称芳基化脱芳构化反应
J Am Chem Soc. 2024 Dec 18;146(50):34970-34978. doi: 10.1021/jacs.4c14754. Epub 2024 Dec 4.
2
Regioselective Substitution of BINOL.联萘酚的区域选择性取代
Chem Rev. 2024 May 22;124(10):6643-6689. doi: 10.1021/acs.chemrev.4c00132. Epub 2024 May 9.
3
Csp-H functionalization of phenols: an effective access route to valuable materials Csp-C bond formation.酚类的Csp-H官能团化：形成Csp-C键从而获得有价值材料的有效途径
Chem Sci. 2024 Feb 21;15(11):3831-3871. doi: 10.1039/d4sc00687a. eCollection 2024 Mar 13.
4
An efficient and chemoselective method to generate arynes.一种生成芳炔的高效且化学选择性方法。
Chem Sci. 2023 Nov 17;14(47):13885-13892. doi: 10.1039/d3sc05429b. eCollection 2023 Dec 6.
5
Recent Advances in Regioselective C-H Bond Functionalization of Free Phenols.近期关于游离酚的区域选择性 C-H 键功能化的进展。
Molecules. 2023 Apr 12;28(8):3397. doi: 10.3390/molecules28083397.
6
3-sulfonyloxyaryl(mesityl)iodonium triflates as 1,2-benzdiyne precursors with activation via ortho-deprotonative elimination strategy.3-磺酰氧基芳基(均三甲苯基)碘𬭩三氟甲磺酸酯作为 1,2-苯二炔前体，通过邻位去质子消除策略进行活化。
Nat Commun. 2023 Apr 3;14(1):1841. doi: 10.1038/s41467-023-37196-3.
7
Cyclic Diaryl λ-Chloranes: Reagents and Their C-C and C-O Couplings with Phenols Aryne Intermediates.环状二芳基 λ-氯代烷：试剂及其与酚的 C-C 和 C-O 偶联反应 芳炔中间体。
J Am Chem Soc. 2023 Jan 11;145(1):345-358. doi: 10.1021/jacs.2c10090. Epub 2022 Dec 19.
8
Modular bismacycles for the selective C-H arylation of phenols and naphthols.用于酚类和萘酚选择性 C-H 芳基化的模块双环。
Nat Chem. 2020 Mar;12(3):260-269. doi: 10.1038/s41557-020-0425-4. Epub 2020 Feb 27.
9
1,2-Bis(arylthio)arene synthesis via aryne intermediates.通过芳炔中间体合成1,2-双（芳硫基）芳烃。
Chem Commun (Camb). 2019 Aug 7;55(64):9467-9470. doi: 10.1039/c9cc03863a.
10
Sydnone-Based Approach to Heterohelicenes through 1,3-Dipolar-Cycloadditions.基于 sydnone 的杂环并苯通过 1,3-偶极环加成反应的合成方法。
J Am Chem Soc. 2019 Jan 30;141(4):1435-1440. doi: 10.1021/jacs.8b11465. Epub 2019 Jan 15.
本文引用的文献
1
Ruthenium-catalyzed C-H bond arylations of arenes bearing removable directing groups via six-membered ruthenacycles.钌催化的含可去除导向基团芳基的 C-H 键芳基化反应通过六元钌环进行。
Org Lett. 2012 Feb 17;14(4):1154-7. doi: 10.1021/ol3000876. Epub 2012 Feb 7.
2
Efficient anodic and direct phenol-arene C,C cross-coupling: the benign role of water or methanol.高效阳极直接苯酚-芳环 C,C 交叉偶联：水或甲醇的良性作用。
J Am Chem Soc. 2012 Feb 22;134(7):3571-6. doi: 10.1021/ja211005g. Epub 2012 Feb 13.
3
Transition-metal-free direct arylation of anilines.无过渡金属催化的苯胺直接芳基化反应。
Angew Chem Int Ed Engl. 2012 Jan 23;51(4):1006-9. doi: 10.1002/anie.201106150. Epub 2011 Dec 12.
4
Helicenes: synthesis and applications.螺旋烯：合成与应用
Chem Rev. 2012 Mar 14;112(3):1463-535. doi: 10.1021/cr200087r. Epub 2011 Oct 24.
5
Mechanisms of osteoclastogenesis inhibition by a novel class of biphenyl-type cannabinoid CB(2) receptor inverse agonists.新型联苯类大麻素CB(2)受体反向激动剂抑制破骨细胞生成的机制
Chem Biol. 2011 Aug 26;18(8):1053-64. doi: 10.1016/j.chembiol.2011.05.012.
6
Transition-metal-free alkynylation of aryl chlorides.无过渡金属参与的芳基氯代烃炔基化反应。
Org Lett. 2011 Aug 19;13(16):4172-5. doi: 10.1021/ol2014736. Epub 2011 Jul 25.
7
Chemical-stimuli-controllable circularly polarized luminescence from anion-responsive π-conjugated molecules.阴离子响应的π共轭分子的化学刺激可控圆偏振发光。
J Am Chem Soc. 2011 Jun 22;133(24):9266-9. doi: 10.1021/ja203206g. Epub 2011 May 25.
8
Base-mediated intermolecular sp2 C-H bond arylation via benzyne intermediates.通过苯炔中间体实现的基于基底的 sp2 C-H 键的分子间芳基化反应。
J Am Chem Soc. 2011 Mar 30;133(12):4243-5. doi: 10.1021/ja200184b. Epub 2011 Mar 8.
9
Well-defined air-stable palladium HASPO complexes for efficient Kumada-Corriu cross-couplings of (hetero)aryl or alkenyl tosylates.用于高效 Kumada-Corriu 交叉偶联（杂芳基）或烯基对甲苯磺酸盐的定义明确的空气稳定钯 HASPO 配合物。
Chemistry. 2011 Mar 1;17(10):2965-71. doi: 10.1002/chem.201002386. Epub 2011 Feb 3.
10
A highly para-selective copper(II)-catalyzed direct arylation of aniline and phenol derivatives.一种高度对位选择性的铜（II）催化的苯胺和苯酚衍生物的直接芳基化反应。
Angew Chem Int Ed Engl. 2011 Jan 10;50(2):458-62. doi: 10.1002/anie.201004703.
Zotero 插件