钯催化甲基磺酰胺与芳基氯的α-芳基化反应
Palladium-Catalyzed α-Arylation of Methyl Sulfonamides with Aryl Chlorides.
作者信息
Zheng Bing, Li Minyan, Gao Gui, He Yuying, Walsh Patrick J
机构信息
Department of Applied Chemistry, China Agricultural University, Beijing 100193, P. R. China; Roy and Diana Vagelos Laboratories, Penn/Merck Laboratory for High-Throughput Experimentation, Department of Chemistry, University of Pennsylvania, 231 South 34th Street, Philadelphia, Pennsylvania 19104-6323, United States.
Roy and Diana Vagelos Laboratories, Penn/Merck Laboratory for High-Throughput Experimentation, Department of Chemistry, University of Pennsylvania, 231 South 34th Street, Philadelphia, Pennsylvania 19104-6323, United States.
出版信息
Adv Synth Catal. 2016 Jun 30;358(13):2156-2162. doi: 10.1002/adsc.201600090. Epub 2016 Jun 15.
Abstract
A Palladium-catalyzed α-arylation of sulfonamides with aryl chlorides is presented. A Buchwald type precatalyst formed with Kwong's indole-based ligand enabled this transformation to be compatible with a large variety of methyl sulfonamides and aryl chlorides in good to excellent yields. Importantly, under the optimized reaction conditions, only mono-arylated products were observed. This method has been applied to the efficient synthesis of sumatriptan, which is used to treat migraines.
摘要
本文介绍了一种钯催化的磺酰胺与芳基氯的α-芳基化反应。由邝氏吲哚基配体形成的布赫瓦尔德型预催化剂使这种转化能够与多种甲基磺酰胺和芳基氯兼容，产率良好至优异。重要的是，在优化的反应条件下，仅观察到单芳基化产物。该方法已应用于用于治疗偏头痛的舒马曲坦的高效合成。
相似文献
1
Palladium-Catalyzed α-Arylation of Methyl Sulfonamides with Aryl Chlorides.钯催化甲基磺酰胺与芳基氯的α-芳基化反应
Adv Synth Catal. 2016 Jun 30;358(13):2156-2162. doi: 10.1002/adsc.201600090. Epub 2016 Jun 15.
2
A General and Practical Palladium-Catalyzed Direct α-Arylation of Amides with Aryl Halides.钯催化酰胺与芳基卤化物的通用且实用的直接α-芳基化反应
Adv Synth Catal. 2014 Jan 13;356(1):165-178. doi: 10.1002/adsc.201300851.
3
N-heterocyclic carbene-palladium(II)-1-methylimidazole complex catalyzed α-arylation reactions of tetralones with aryl chlorides and further transformation of the products.N-杂环卡宾-钯（II）-1-甲基咪唑配合物催化四氢萘酮与芳基氯的α-芳基化反应及产物的进一步转化。
Org Biomol Chem. 2015 Sep 14;13(34):9012-21. doi: 10.1039/c5ob01203a. Epub 2015 Jul 27.
4
A new strategy for the synthesis of benzylic sulfonamides: palladium-catalyzed arylation and sulfonamide metathesis.一种合成苄基磺酰胺的新策略：钯催化芳基化和磺酰胺复分解反应。
J Org Chem. 2007 Oct 12;72(21):8135-8. doi: 10.1021/jo701431j. Epub 2007 Sep 20.
5
Direct C-H bond arylation of fluorenes with aryl chlorides catalyzed by N-heterocyclic carbene-palladium(II)-1-methylimidazole complex and further transformation of the products in a one-pot procedure.N-杂环卡宾-钯（II）-1-甲基咪唑配合物催化芴与芳基氯的直接C-H键芳基化反应以及产物在一锅法中的进一步转化。
Org Biomol Chem. 2014 Nov 14;12(42):8488-98. doi: 10.1039/c4ob01594k.
6
Ligand Control of Palladium-Catalyzed Site-Selective α- and γ-Arylation of α,β-Unsaturated Ketones with (Hetero)aryl Halides.配体对钯催化的α,β-不饱和酮与（杂）芳基卤化物的位点选择性α-和γ-芳基化反应的控制
Angew Chem Int Ed Engl. 2020 Dec 21;59(52):23438-23444. doi: 10.1002/anie.202010682. Epub 2020 Nov 5.
7
Palladium-catalyzed direct intermolecular α-arylation of amides with aryl chlorides.钯催化的酰胺与芳基氯的直接分子间 α-芳基化反应。
Org Lett. 2013 Aug 16;15(16):4190-3. doi: 10.1021/ol4019002. Epub 2013 Aug 5.
8
N-Heterocyclic carbene-palladium(ii)-1-methylimidazole complex catalyzed direct C-H bond arylation of imidazo[1,2-a]pyridines with aryl chlorides.N-杂环卡宾-钯（II）-1-甲基咪唑配合物催化咪唑并[1,2-a]吡啶与芳基氯的直接C-H键芳基化反应。
Org Biomol Chem. 2017 Feb 1;15(5):1151-1154. doi: 10.1039/c6ob02704k.
9
Palladium-catalyzed direct α-arylation of methyl sulfones with aryl bromides.钯催化的甲基砜与芳基溴化物的直接 α-芳基化反应。
Org Lett. 2013 Apr 5;15(7):1690-3. doi: 10.1021/ol400472v. Epub 2013 Mar 21.
10
Palladium-catalyzed direct arylation of methyl sulfoxides with aryl halides.钯催化的甲基亚砜与芳基卤化物的直接芳基化反应。
J Am Chem Soc. 2013 Mar 13;135(10):3740-3. doi: 10.1021/ja4009776. Epub 2013 Feb 27.
引用本文的文献
1
Chemical synthesis, inhibitory activity and molecular mechanism of 1-deoxynojirimycin-chrysin as a potent α-glucosidase inhibitor.1-脱氧野尻霉素-白杨素作为一种有效的α-葡萄糖苷酶抑制剂的化学合成、抑制活性及分子机制
RSC Adv. 2021 Dec 1;11(61):38703-38711. doi: 10.1039/d1ra07753h. eCollection 2021 Nov 29.
2
A domino reaction for generating β-aryl aldehydes from alkynes by substrate recognition catalysis.通过底物识别催化，从炔烃生成β-芳基醛的级联反应。
Nat Commun. 2019 Oct 25;10(1):4868. doi: 10.1038/s41467-019-12770-w.
3
Arylation of Azaarylmethylamines with Aryl Chlorides and a NiBr/NIXANTPHOS-based Catalyst.氮杂芳基甲胺与芳基氯及基于NiBr/NIXANTPHOS的催化剂的芳基化反应
Adv Synth Catal. 2017 Aug 17;359(16):2890-2894. doi: 10.1002/adsc.201700438. Epub 2017 Jul 12.
4
Biointeractions of Herbicide Atrazine with Human Serum Albumin: UV-Vis, Fluorescence and Circular Dichroism Approaches.除草剂阿特拉津与人血清白蛋白的生物相互作用：紫外可见、荧光和圆二色性方法。
Int J Environ Res Public Health. 2018 Jan 11;15(1):116. doi: 10.3390/ijerph15010116.
5
Transition-Metal-Free Radical C(sp)-C(sp) and C(sp)-C(sp) Coupling Enabled by 2-Azaallyls as Super-Electron-Donors and Coupling-Partners.无金属自由基 C(sp)-C(sp)和 C(sp)-C(sp)键偶联反应：2-氮杂烯丙基作为超电子给体和偶联伙伴。
J Am Chem Soc. 2017 Nov 15;139(45):16327-16333. doi: 10.1021/jacs.7b09394. Epub 2017 Oct 31.
6
Palladium-Catalyzed Selective α-Alkenylation of Pyridylmethyl Ethers with Vinyl Bromides.钯催化吡啶甲基醚与溴代乙烯的选择性 α-烯丙基化反应。
Org Lett. 2016 May 20;18(10):2371-4. doi: 10.1021/acs.orglett.6b00815. Epub 2016 May 10.
本文引用的文献
1
Umpolung Synthesis of Diarylmethylamines via Palladium-Catalyzed Arylation of -Benzyl Aldimines.通过钯催化的α-苄基亚胺的芳基化反应实现二芳基甲胺的极性反转合成
Adv Synth Catal. 2016 Jun 16;358(12):1910-1915. doi: 10.1002/adsc.201600075. Epub 2016 May 12.
2
Palladium-Catalyzed C-H Arylation of α,β-Unsaturated Imines: Catalyst-Controlled Synthesis of Enamine and Allylic Amine Derivatives.钯催化的α,β-不饱和亚胺的C-H芳基化反应：催化剂控制的烯胺和烯丙基胺衍生物的合成
Angew Chem Int Ed Engl. 2016 Feb 18;55(8):2825-9. doi: 10.1002/anie.201509757. Epub 2016 Feb 5.
3
Palladium-catalyzed C(sp(3))-H Arylation of N-Boc benzylalkylamines via a deprotonative cross-coupling process.钯催化的N-叔丁氧羰基苄基烷基胺通过去质子化交叉偶联过程实现的C(sp(3))-H芳基化反应
Chemistry. 2015 Jul 27;21(31):11010-3. doi: 10.1002/chem.201502017. Epub 2015 Jun 30.
4
Synthesis of Heteroaryl Sulfonamides from Organozinc Reagents and 2,4,6-Trichlorophenyl Chlorosulfate.从有机锌试剂和 2,4,6-三氯苯基氯磺酰酯合成杂芳基砜酰胺。
Org Lett. 2015 Jun 19;17(12):3170-3. doi: 10.1021/acs.orglett.5b01540. Epub 2015 Jun 11.
5
Natural Product Primary Sulfonamides and Primary Sulfamates.天然产物伯磺酰胺和伯氨基磺酸酯。
J Nat Prod. 2015 Jun 26;78(6):1470-7. doi: 10.1021/np501015m. Epub 2015 Jun 2.
6
Palladium catalyzed diaryl sulfoxide generation from aryl benzyl sulfoxides and aryl chlorides.钯催化由芳基苄基亚砜和芳基氯化物生成二芳基亚砜。
Org Lett. 2015 Mar 6;17(5):1168-71. doi: 10.1021/acs.orglett.5b00092. Epub 2015 Feb 16.
7
Convenient route to secondary sulfinates: application to the stereospecific synthesis of α-C-chiral sulfonamides.合成仲亚磺酸盐的便捷方法：应用于α-C-手性磺酰胺的立体定向合成
Org Lett. 2014 Dec 5;16(23):6248-51. doi: 10.1021/ol503208z. Epub 2014 Nov 21.
8
Synthesis of diarylmethylamines palladium-catalyzed regioselective arylation of 1,1,3-triaryl-2-azaallyl anions.二芳基甲胺的合成：钯催化1,1,3-三芳基-2-氮杂烯丙基阴离子的区域选择性芳基化反应。
Chem Sci. 2014 Jun 1;5(6):2383-2391. doi: 10.1039/C3SC53526F.
9
Stereoconvergent arylations and alkenylations of unactivated alkyl electrophiles: catalytic enantioselective synthesis of secondary sulfonamides and sulfones.未活化烷基亲电试剂的立体汇聚芳基化和烯基化反应：仲磺酰胺和砜的催化对映选择性合成
J Am Chem Soc. 2014 Aug 27;136(34):12161-5. doi: 10.1021/ja506885s. Epub 2014 Aug 15.
10
Palladium-catalyzed regioselective arylation of 1,1,3-triaryl-2-azaallyl anions with aryl chlorides.钯催化的1,1,3-三芳基-2-氮杂烯丙基阴离子与芳基氯化物的区域选择性芳基化反应。
Org Lett. 2014 Aug 15;16(16):4312-5. doi: 10.1021/ol502043j. Epub 2014 Aug 5.
Zotero 插件