铁催化的芳基磺酸盐和氨基甲酸酯的烷基化反应。
Iron-catalyzed alkylations of aryl sulfamates and carbamates.
机构信息
Department of Chemistry and Biochemistry, University of California , Los Angeles, California 90095-1569, United States.
出版信息
Org Lett. 2012 Jul 20;14(14):3796-9. doi: 10.1021/ol301681z. Epub 2012 Jul 3.
Abstract
The alkylation of aryl sulfamates and carbamates using iron catalysis is reported. The method constructs sp(2)-sp(3) carbon-carbon bonds and provides synthetically useful yields across a range of substrates (>35 examples). The directing group ability of sulfamates and carbamates, accompanied by their low reactivity toward conventional cross-couplings, renders these substrates useful for the synthesis of polyfunctionalized arenes.
摘要
本文报道了铁催化的芳基磺酰胺和氨基甲酸酯的烷基化反应。该方法构建了 sp(2)-sp(3) 碳-碳键，在一系列底物中提供了具有合成实用性的产率（>35 个实例）。磺酰胺和氨基甲酸酯的导向基团能力，以及它们对常规交叉偶联反应的低反应性，使得这些底物可用于多官能化芳基的合成。
相似文献
1
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.
2
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.
3
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.
4
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.
5
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.
6
Cobalt-catalyzed direct arylation and benzylation by C-H/C-O cleavage with sulfamates, carbamates, and phosphates.钴催化的通过与氨基磺酸酯、氨基甲酸酯和磷酸酯进行C-H/C-O裂解实现的直接芳基化和苄基化反应。
Angew Chem Int Ed Engl. 2012 Aug 13;51(33):8251-4. doi: 10.1002/anie.201202466. Epub 2012 Jul 12.
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
Three-component, room temperature crotylation catalyzed by solid-supported Brønsted acid: enantioselective synthesis of homoallylic carbamates.固体负载布朗斯特酸催化的三组分室温巴豆酰化反应：高烯丙基氨基甲酸酯的对映选择性合成
Org Lett. 2005 Oct 13;7(21):4701-4. doi: 10.1021/ol051885s.
9
Pd-Catalyzed Suzuki-Miyaura and Hiyama-Denmark Couplings of Aryl Sulfamates.钯催化的芳基磺酸盐的铃木-宫浦偶联反应和 Hiyama-Denmark 偶联反应。
Org Lett. 2016 Nov 18;18(22):5784-5787. doi: 10.1021/acs.orglett.6b02330. Epub 2016 Nov 3.
10
Iron-Catalyzed Stereoselective Cross-Coupling Reactions of Stereodefined Enol Carbamates with Grignard Reagents.铁催化的立体定义的烯醇氨基甲酸酯与格氏试剂的立体选择性交叉偶联反应。
Angew Chem Int Ed Engl. 2016 Jun 1;55(23):6689-93. doi: 10.1002/anie.201601899. Epub 2016 Apr 18.
引用本文的文献
1
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.
2
Enantioselective alkylative cross-coupling of unactivated aromatic C-O electrophiles.非活化芳族 C-O 亲电试剂的对映选择性烷基化交叉偶联。
Nat Commun. 2022 May 26;13(1):2953. doi: 10.1038/s41467-022-30693-x.
3
Iron-catalysed allylation-hydrogenation sequences as masked alkyl-alkyl cross-couplings.铁催化的烯丙基化-氢化序列作为掩蔽的烷基-烷基交叉偶联反应。
RSC Adv. 2019 Oct 2;9(54):31217-31223. doi: 10.1039/c9ra07604b. eCollection 2019 Oct 1.
4
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.
5
Photochemically-Mediated, Nickel-Catalyzed Synthesis of -(Hetero)aryl Sulfamate Esters.光化学-镍催化合成 -(杂)芳基磺酰胺酯。
Org Lett. 2019 Sep 6;21(17):7049-7054. doi: 10.1021/acs.orglett.9b02621. Epub 2019 Aug 22.
6
Combined Effects of Backbone and N-Substituents on Structure, Bonding, and Reactivity of Alkylated Iron(II)-NHCs.主链和N-取代基对烷基化铁（II）-氮杂环卡宾的结构、键合及反应活性的综合影响
Organometallics. 2018 Sep 24;37(18):3093-3101. doi: 10.1021/acs.organomet.8b00466. Epub 2018 Sep 6.
7
NHC and nucleophile chelation effects on reactive iron(ii) species in alkyl-alkyl cross-coupling.NHC与亲核试剂对烷基-烷基交叉偶联中活性铁（II）物种的螯合作用。
Chem Sci. 2018 Jan 8;9(7):1878-1891. doi: 10.1039/c7sc04750a. eCollection 2018 Feb 21.
8
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.
9
Pd-catalyzed Suzuki-Miyaura cross-coupling reactions between sulfamates and potassium Boc-protected aminomethyltrifluoroborates.钯催化的磺酸盐与 Boc 保护的氨甲基三氟硼酸钾之间的 Suzuki-Miyaura 交叉偶联反应。
Org Lett. 2013 May 17;15(10):2534-7. doi: 10.1021/ol401021x. Epub 2013 May 6.
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
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.
3
The development of bulky palladium NHC complexes for the most-challenging cross-coupling reactions.用于最具挑战性的交叉偶联反应的大体积钯 NHC 配合物的开发。
Angew Chem Int Ed Engl. 2012 Apr 2;51(14):3314-32. doi: 10.1002/anie.201106131. Epub 2012 Jan 27.
4
Trace metal impurities in catalysis.催化中的痕量金属杂质。
Chem Soc Rev. 2012 Feb 7;41(3):979-87. doi: 10.1039/c2cs15249e. Epub 2012 Jan 4.
5
Iron-catalyzed C-H bond activation for the ortho-arylation of aryl pyridines and imines with Grignard reagents.铁催化的 C-H 键活化用于芳基吡啶和亚胺与格氏试剂的邻位芳基化反应。
Chem Asian J. 2011 Nov 4;6(11):3059-65. doi: 10.1002/asia.201100470. Epub 2011 Sep 6.
6
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.
7
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.
8
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.
9
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.
10
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.
Zotero 插件