氧化还原中性的芳基化反应。
Redox-neutral α-arylation of amines.
机构信息
Department of Chemistry and Chemical Biology, Rutgers, The State University of New Jersey , Piscataway, New Jersey 08854, United States.
出版信息
Org Lett. 2014 Feb 7;16(3):730-2. doi: 10.1021/ol403431u. Epub 2013 Dec 13.
Abstract
The direct α-arylation/N-alkylation of cyclic amines was achieved in a redox-neutral fashion under mild conditions. Transformations occur in the absence of any additives or are promoted by simple carboxylic acids.
摘要
在温和条件下，通过氧化还原中性方式实现了环状胺的直接α-芳基化/N-烷基化。这些转化在没有任何添加剂的情况下发生，或者在简单的羧酸的促进下发生。
相似文献
1
Redox-neutral α-arylation of amines.氧化还原中性的芳基化反应。
Org Lett. 2014 Feb 7;16(3):730-2. doi: 10.1021/ol403431u. Epub 2013 Dec 13.
2
Facile N-arylation of amines and sulfonamides and o-arylation of phenols and arenecarboxylic acids.胺和磺酰胺的简便N-芳基化以及酚和芳酸的邻位芳基化。
J Org Chem. 2006 Apr 14;71(8):3198-209. doi: 10.1021/jo0602221.
3
Boron-Catalyzed N-Alkylation of Amines using Carboxylic Acids.硼催化羧酸对胺的 N-烷基化反应。
Angew Chem Int Ed Engl. 2015 Jul 27;54(31):9042-6. doi: 10.1002/anie.201503879. Epub 2015 Jul 6.
4
N-Alkylation Using Sodium Triacetoxyborohydride with Carboxylic Acids as Alkyl Sources.以羧酸为烷基源，使用三乙酰氧基硼氢化钠进行N-烷基化反应。
Chem Pharm Bull (Tokyo). 2018;66(1):101-103. doi: 10.1248/cpb.c17-00716.
5
Redox-neutral α-cyanation of amines.氧化还原中性α-氰化胺。
J Am Chem Soc. 2012 Sep 19;134(37):15305-8. doi: 10.1021/ja308009g. Epub 2012 Sep 11.
6
C-H functionalization of cyclic amines: redox-annulations with α,β-unsaturated carbonyl compounds.环胺的碳-氢官能团化：与α,β-不饱和羰基化合物的氧化还原环化反应
Chem Commun (Camb). 2015 Jul 7;51(53):10648-51. doi: 10.1039/c5cc03390j.
7
Redox-neutral copper(II) carboxylate catalyzed α-alkynylation of amines.氧化还原中性铜（II）羧酸盐催化的胺的α-炔基化反应。
Angew Chem Int Ed Engl. 2013 Mar 25;52(13):3765-9. doi: 10.1002/anie.201300021. Epub 2013 Feb 25.
8
Driving Recursive Dehydration by P/P Catalysis: Annulation of Amines and Carboxylic Acids by Sequential C-N and C-C Bond Formation.通过 P/P 催化驱动的递归脱水反应：通过顺序 C-N 和 C-C 键形成实现胺和羧酸的环化反应。
J Am Chem Soc. 2019 Aug 14;141(32):12507-12512. doi: 10.1021/jacs.9b06277. Epub 2019 Jul 30.
9
The azomethine ylide route to amine C-H functionalization: redox-versions of classic reactions and a pathway to new transformations.通往胺C-H官能化的甲亚胺叶立德途径：经典反应的氧化还原版本及新转化途径
Acc Chem Res. 2015 Feb 17;48(2):317-28. doi: 10.1021/ar5003768. Epub 2015 Jan 6.
10
Direct catalytic N-alkylation of amines with carboxylic acids.胺与羧酸的直接催化 N-烷基化反应。
J Am Chem Soc. 2014 Oct 8;136(40):14314-9. doi: 10.1021/ja5093612. Epub 2014 Sep 29.
引用本文的文献
1
Redox-neutral α-functionalization of pyrrolidines: facile access to α-aryl-substituted pyrrolidines.吡咯烷的氧化还原中性α-官能团化：简便合成α-芳基取代吡咯烷的方法。
RSC Adv. 2024 Apr 15;14(17):11986-11991. doi: 10.1039/d4ra00983e. eCollection 2024 Apr 10.
2
Strategies Toward the Catalyst-Free α-C-H Functionalizations of Tertiary Amines.无催化剂条件下叔胺的α-C-H 官能化反应策略。
Top Curr Chem (Cham). 2023 May 3;381(4):14. doi: 10.1007/s41061-023-00424-x.
3
Copper-catalyzed aerobic decarboxylative coupling between cyclic α-amino acids and diverse C-H nucleophiles with low catalyst loading.铜催化的环状α-氨基酸与多种C-H亲核试剂之间的需氧脱羧偶联反应，催化剂负载量低。
RSC Adv. 2018 May 1;8(29):16202-16206. doi: 10.1039/c8ra02340a. eCollection 2018 Apr 27.
4
Condensation-Based Methods for the C-H Bond Functionalization of Amines.基于缩合反应的胺类C-H键官能团化方法
Synthesis (Stuttg). 2021 Nov;53(21):3869-3908. doi: 10.1055/a-1631-2140. Epub 2021 Sep 2.
5
C-H Bond Functionalization of Amines: A Graphical Overview of Diverse Methods.胺的C-H键官能团化：多种方法的图形概述
SynOpen. 2021;5(3):173-228. doi: 10.1055/s-0040-1706051. Epub 2021 Aug 12.
6
Redox-Annulations of Cyclic Amines with 2-(2-Oxoethyl)malonates.环状胺与 2-(2-氧代乙基)丙二酸酯的氧化环化反应。
Org Lett. 2018 Jul 6;20(13):4090-4093. doi: 10.1021/acs.orglett.8b01642. Epub 2018 Jun 25.
7
Acetic Acid Promoted Redox Annulations with Dual C-H Functionalization.乙酸促进具有双重 C-H 功能化的氧化还原环化反应。
Org Lett. 2017 Jun 2;19(11):2841-2844. doi: 10.1021/acs.orglett.7b01047. Epub 2017 May 16.
8
Redox-Neutral Aromatization of Cyclic Amines: Mechanistic Insights and Harnessing of Reactive Intermediates for Amine α- and β-C-H Functionalization.环状胺的氧化还原中性芳构化：反应机理见解及利用反应中间体实现胺α-和β-C-H官能化
Chemistry. 2016 Dec 12;22(50):18179-18189. doi: 10.1002/chem.201603839. Epub 2016 Nov 9.
9
Asymmetric Redox-Annulation of Cyclic Amines.环状胺的不对称氧化还原环化反应
J Org Chem. 2015 Oct 2;80(19):9628-40. doi: 10.1021/acs.joc.5b01384.
10
Intramolecular Redox-Mannich Reactions: Facile Access to the Tetrahydroprotoberberine Core.分子内氧化还原-曼尼希反应：便捷合成四氢原小檗碱核心结构
Chemistry. 2015 Sep 7;21(37):12908-13. doi: 10.1002/chem.201501667. Epub 2015 Jul 28.
本文引用的文献
1
Enantioselective double manipulation of tetrahydroisoquinolines with terminal alkynes and aldehydes under copper(I) catalysis.铜（I）催化下末端炔烃和醛对四氢异喹啉的对映选择性双重操作。
Angew Chem Int Ed Engl. 2014 Jan 3;53(1):277-81. doi: 10.1002/anie.201308699. Epub 2013 Nov 29.
2
CuI-catalyzed C1-alkynylation of tetrahydroisoquinolines (THIQs) by A3 reaction with tunable iminium ions.铜催化四氢异喹啉（THIQs）通过 A3 反应与可调变亚胺离子的 C1-炔基化反应。
Org Lett. 2013 Dec 6;15(23):5928-31. doi: 10.1021/ol402517e. Epub 2013 Nov 15.
3
Facile Access to Ring-Fused Aminals via Direct α-Amination of Secondary Amines with -Aminobenzaldehydes. Synthesis of Vasicine, Deoxyvasicine, Deoxyvasicinone, Mackinazolinone and Ruteacarpine.通过仲胺与α-氨基苯甲醛的直接α-胺化反应简便合成稠环缩醛胺。鸭嘴花碱、去氧鸭嘴花碱、去氧鸭嘴花酮碱、麦金鸡唑啉酮和吴茱萸次碱的合成。
Synthesis (Stuttg). 2013 Oct 6;45(13):1430-1748.
4
The redox-neutral approach to C-H functionalization.C-H 键功能化的氧化还原中性方法。
Chemistry. 2013 Sep 27;19(40):13274-87. doi: 10.1002/chem.201301522. Epub 2013 Sep 11.
5
Redox-neutral α-C-H bond functionalization of secondary amines with concurrent C-P bond formation/N-alkylation.通过同时形成 C-P 键/ N-烷基化反应实现仲胺的氧化还原中性 α-C-H 键官能化。
Org Lett. 2013 Sep 6;15(17):4358-61. doi: 10.1021/ol401858k. Epub 2013 Aug 19.
6
Simple and direct sp3 C-H bond arylation of tetrahydroisoquinolines and isochromans via 2,3-dichloro-5,6-dicyano-1,4-benzoquinone oxidation under mild conditions.温和条件下通过 2,3-二氯-5,6-二氰基-1,4-苯醌氧化实现四氢异喹啉和异色满的 sp3 C-H 键芳基化反应，过程简单直接。
Org Lett. 2013 Jul 19;15(14):3650-3. doi: 10.1021/ol401534g. Epub 2013 Jul 1.
7
Ruthenium-catalyzed α-(hetero)arylation of saturated cyclic amines: reaction scope and mechanism.钌催化的饱和环状胺的α-（杂）芳基化反应：反应范围和机理。
Chemistry. 2013 Jul 29;19(31):10378-87. doi: 10.1002/chem.201204438. Epub 2013 Jun 18.
8
Simple and sustainable iron-catalyzed aerobic C-H functionalization of N,N-dialkylanilines.简单可持续的铁催化有氧 N,N-二烷基苯胺 C-H 官能化反应。
J Am Chem Soc. 2013 Jun 26;135(25):9475-9. doi: 10.1021/ja402479r. Epub 2013 Jun 14.
9
Metal-free α-amination of secondary amines: computational and experimental evidence for azaquinone methide and azomethine ylide intermediates.无金属的仲胺的α-胺化反应：氮宾甲烷和亚胺叶立德中间体的计算和实验证据。
J Org Chem. 2013 Apr 19;78(8):4132-44. doi: 10.1021/jo400483h. Epub 2013 Apr 2.
10
Cascade hydroamination/redox reaction for the synthesis of cyclic aminals catalyzed by a combined gold complex and Brønsted acid.级联氢胺化/氧化还原反应在金配合物和布朗斯特酸共同催化下合成环状脒。
Chemistry. 2013 Apr 22;19(17):5232-7. doi: 10.1002/chem.201300052. Epub 2013 Mar 19.
Zotero 插件