镍催化的芳基磺酰胺和氨基甲酸酯的氨化反应，使用一种空气稳定的前催化剂。
Nickel-catalyzed amination of aryl sulfamates and carbamates using an air-stable precatalyst.
机构信息
Department of Chemistry and Biochemistry, University of California, Los Angeles, Los Angeles, California 90095-1569, United States.
出版信息
Org Lett. 2012 Aug 17;14(16):4182-5. doi: 10.1021/ol301847m. Epub 2012 Jul 31.
Abstract
A facile nickel-catalyzed method to achieve the amination of synthetically useful aryl sulfamates and carbamates is reported. Contrary to most Ni-catalyzed amination reactions, this user-friendly approach relies on an air-stable Ni(II) precatalyst, which, when employed with a mild reducing agent, efficiently delivers aminated products in good to excellent yields. The scope of the method is broad with respect to both coupling partners and includes heterocyclic substrates.
摘要
报道了一种简便的镍催化方法，可实现合成上有用的芳基磺酰胺和氨基甲酸酯的胺化反应。与大多数 Ni 催化的胺化反应不同，这种用户友好的方法依赖于空气稳定的 Ni(II)前催化剂，当与温和的还原剂一起使用时，可有效地以良好至优异的收率得到胺化产物。该方法在偶联伙伴方面具有广泛的适用性，包括杂环底物。
相似文献
1
Nickel-catalyzed amination of aryl sulfamates and carbamates using an air-stable precatalyst.镍催化的芳基磺酰胺和氨基甲酸酯的氨化反应，使用一种空气稳定的前催化剂。
Org Lett. 2012 Aug 17;14(16):4182-5. doi: 10.1021/ol301847m. Epub 2012 Jul 31.
2
Development of an air-stable nickel precatalyst for the amination of aryl chlorides, sulfamates, mesylates, and triflates.发展一种用于芳基氯化物、磺酸盐、甲磺酸盐和三氟甲磺酸盐的氨化反应的空气稳定的镍前催化剂。
Org Lett. 2014 Jan 3;16(1):220-3. doi: 10.1021/ol403209k. Epub 2013 Nov 27.
3
Rapid nickel-catalyzed Suzuki-Miyaura cross-couplings of aryl carbamates and sulfamates utilizing microwave heating.利用微波加热快速镍催化的芳基氨基甲酸酯和磺胺酸盐的 Suzuki-Miyaura 交叉偶联反应。
J Org Chem. 2011 Mar 4;76(5):1507-10. doi: 10.1021/jo1024464. Epub 2011 Jan 20.
4
Exploring new uses for C-H amination: Ni-catalyzed cross-coupling of cyclic sulfamates.探索C-H胺化的新用途：镍催化的环状氨基磺酸酯交叉偶联反应。
Org Lett. 2005 Oct 13;7(21):4685-8. doi: 10.1021/ol051896l.
5
Iron-catalyzed alkylations of aryl sulfamates and carbamates.铁催化的芳基磺酸盐和氨基甲酸酯的烷基化反应。
Org Lett. 2012 Jul 20;14(14):3796-9. doi: 10.1021/ol301681z. Epub 2012 Jul 3.
6
Nickel-Catalyzed Amination of Aryl Chlorides and Sulfamates in 2-Methyl-THF.镍催化的芳基氯和氨基磺酸酯在2-甲基四氢呋喃中的胺化反应
ACS Catal. 2014 Sep 5;4(9):3289-3293. doi: 10.1021/cs501045v. Epub 2014 Aug 20.
7
Cine substitution of arenes using the aryl carbamate as a removable directing group.使用芳基氨基甲酸酯作为可去除导向基团的芳基取代反应。
Org Lett. 2012 Jun 1;14(11):2918-21. doi: 10.1021/ol301275u. Epub 2012 May 21.
8
Suzuki-Miyaura coupling of aryl carbamates, carbonates, and sulfamates.铃木-宫浦偶联反应在芳基氨基甲酸酯、碳酸酯和磺酸盐中的应用。
J Am Chem Soc. 2009 Dec 16;131(49):17748-9. doi: 10.1021/ja906477r.
9
Suzuki-Miyaura cross-coupling of aryl carbamates and sulfamates: experimental and computational studies.芳基氨基甲酸酯和磺胺酸盐的铃木-宫浦交叉偶联反应：实验和计算研究。
J Am Chem Soc. 2011 Apr 27;133(16):6352-63. doi: 10.1021/ja200398c. Epub 2011 Apr 1.
10
Nickel-catalyzed amination of aryl sulfamates.镍催化芳基氨基磺酸酯的胺化反应。
Angew Chem Int Ed Engl. 2011 Feb 25;50(9):2171-3. doi: 10.1002/anie.201007325. Epub 2011 Jan 20.
引用本文的文献
1
Metal-N-Heterocyclic Carbene Complexes in Buchwald-Hartwig Amination Reactions.布赫瓦尔德-哈特维希胺化反应中的金属-N-杂环卡宾配合物
Chem Rev. 2025 Jun 25;125(12):5349-5435. doi: 10.1021/acs.chemrev.5c00088. Epub 2025 Jun 6.
2
The Versatile and Strategic -Carbamate Directed Metalation Group in the Synthesis of Aromatic Molecules: An Update.芳香分子合成中多功能且具策略性的——氨基甲酸酯导向金属化基团：最新进展
Chem Rev. 2024 Jun 26;124(12):7731-7828. doi: 10.1021/acs.chemrev.3c00923. Epub 2024 Jun 12.
3
The development of cage phosphine 'DalPhos' ligands to enable nickel-catalyzed cross-couplings of (hetero)aryl electrophiles.用于实现镍催化（杂）芳基亲电试剂交叉偶联的笼状膦配体“DalPhos”的开发。
Chem Sci. 2024 Apr 25;15(20):7394-7407. doi: 10.1039/d4sc01253d. eCollection 2024 May 22.
4
Broad-Scope Amination of Aryl Sulfamates Catalyzed by a Palladium Phosphine Complex.钯膦配合物催化芳基氨基磺酸酯的广域胺化反应
ACS Catal. 2023 Aug 4;13(16):10945-10952. doi: 10.1021/acscatal.3c03166. eCollection 2023 Aug 18.
5
Activation of C-O and C-N Bonds Using Non-Precious-Metal Catalysis.使用非贵金属催化激活碳-氧键和碳-氮键
ACS Catal. 2020 Oct 16;10(20):12109-12126. doi: 10.1021/acscatal.0c03334. Epub 2020 Sep 10.
6
Convenient Method of Synthesizing Aryloxyalkyl Esters from Phenolic Esters Using Halogenated Alcohols.用卤代醇合成芳氧基烷基酯的简便方法。
Molecules. 2018 Jul 13;23(7):1715. doi: 10.3390/molecules23071715.
7
Bright Side of Lignin Depolymerization: Toward New Platform Chemicals.木质素解聚的光明面：迈向新型平台化学品。
Chem Rev. 2018 Jan 24;118(2):614-678. doi: 10.1021/acs.chemrev.7b00588. Epub 2018 Jan 16.
8
Mechanism and Origins of Ligand-Controlled Stereoselectivity of Ni-Catalyzed Suzuki-Miyaura Coupling with Benzylic Esters: A Computational Study.镍催化Suzuki-Miyaura 偶联与苄酯的配体控制立体选择性的机制和起源：计算研究。
J Am Chem Soc. 2017 Sep 20;139(37):12994-13005. doi: 10.1021/jacs.7b04973. Epub 2017 Sep 7.
9
Breaking Amides using Nickel Catalysis.利用镍催化断裂酰胺键
ACS Catal. 2017 Feb 3;7(2):1413-1423. doi: 10.1021/acscatal.6b03277. Epub 2017 Jan 6.
10
A modular, air-stable nickel precatalyst.一种模块化的、空气稳定的镍预催化剂。
Org Lett. 2015 May 1;17(9):2166-9. doi: 10.1021/acs.orglett.5b00766. Epub 2015 Apr 17.
本文引用的文献
1
Nickel-catalyzed amination of aryl carbamates and sequential site-selective cross-couplings.镍催化芳基氨基甲酸酯的胺化反应及连续的位点选择性交叉偶联反应
Chem Sci. 2011 Sep 1;2(9):1766-1771. doi: 10.1039/c1sc00230a. Epub 2011 Jun 9.
2
Comparison of arylboron-based nucleophiles in Ni-catalyzed Suzuki-Miyaura cross-coupling with aryl mesylates and sulfamates.芳基硼酸类亲核试剂在 Ni 催化的芳基甲磺酸酯和芳基磺酸盐的 Suzuki-Miyaura 交叉偶联反应中的比较。
J Org Chem. 2012 Jul 20;77(14):5956-64. doi: 10.1021/jo300547v. Epub 2012 Jun 29.
3
Ni(COD)2/PCy3 catalyzed cross-coupling of aryl and heteroaryl neopentylglycolboronates with aryl and heteroaryl mesylates and sulfamates in THF at room temperature.Ni(COD)2/PCy3 催化的芳基和杂芳基新戊二醇硼酸酯与芳基和杂芳基甲磺酸酯和磺酸盐在室温下的 THF 中的交叉偶联。
J Org Chem. 2011 Dec 16;76(24):9946-55. doi: 10.1021/jo202037x. Epub 2011 Nov 16.
4
Rhodium-catalyzed direct ortho C-H olefination of phenol derivatives.铑催化的酚类衍生物的直接邻位 C-H 烯烃化反应。
Chem Commun (Camb). 2011 Oct 7;47(37):10458-60. doi: 10.1039/c1cc14108b. Epub 2011 Aug 18.
5
Rhodium-catalyzed selective C-H activation/olefination of phenol carbamates.铑催化的酚氨基甲酸酯的选择性 C-H 活化/烯烃化反应。
Org Lett. 2011 Jun 17;13(12):3235-7. doi: 10.1021/ol201140q. Epub 2011 May 23.
6
Suzuki-Miyaura cross-coupling of aryl carbamates and sulfamates: experimental and computational studies.芳基氨基甲酸酯和磺胺酸盐的铃木-宫浦交叉偶联反应：实验和计算研究。
J Am Chem Soc. 2011 Apr 27;133(16):6352-63. doi: 10.1021/ja200398c. Epub 2011 Apr 1.
7
Palladium- and nickel-catalyzed aminations of aryl imidazolylsulfonates and sulfamates.钯和镍催化的芳基咪唑基磺酸盐和磺酰胺的胺化反应。
Org Lett. 2011 Apr 1;13(7):1784-6. doi: 10.1021/ol200267b. Epub 2011 Feb 25.
8
Nickel-catalyzed amination of aryl sulfamates.镍催化芳基氨基磺酸酯的胺化反应。
Angew Chem Int Ed Engl. 2011 Feb 25;50(9):2171-3. doi: 10.1002/anie.201007325. Epub 2011 Jan 20.
9
Activation of "inert" alkenyl/aryl C-O bond and its application in cross-coupling reactions.“惰性”烯基/芳基 C-O 键的活化及其在交叉偶联反应中的应用。
Chemistry. 2011 Feb 7;17(6):1728-59. doi: 10.1002/chem.201002273. Epub 2011 Jan 17.
10
Rapid nickel-catalyzed Suzuki-Miyaura cross-couplings of aryl carbamates and sulfamates utilizing microwave heating.利用微波加热快速镍催化的芳基氨基甲酸酯和磺胺酸盐的 Suzuki-Miyaura 交叉偶联反应。
J Org Chem. 2011 Mar 4;76(5):1507-10. doi: 10.1021/jo1024464. Epub 2011 Jan 20.
Zotero 插件