α-氨基酸的双催化脱羧烯丙基化反应及其不同反应机理
Dual Catalytic Decarboxylative Allylations of α-Amino Acids and Their Divergent Mechanisms.
作者信息
Lang Simon B, O'Nele Kathryn M, Douglas Justin T, Tunge Jon A
机构信息
Department of Chemistry, The University of Kansas, 2010 Malott Hall, 1251 Wescoe Hall Drive, Lawrence KS 66045 (USA).
出版信息
Chemistry. 2015 Dec 14;21(51):18589-93. doi: 10.1002/chem.201503644. Epub 2015 Nov 3.
Abstract
The room temperature radical decarboxylative allylation of N-protected α-amino acids and esters has been accomplished via a combination of palladium and photoredox catalysis to provide homoallylic amines. Mechanistic investigations revealed that the stability of the α-amino radical, which is formed by decarboxylation, dictates the predominant reaction pathway between competing mechanisms.
摘要
通过钯催化和光氧化还原催化相结合的方法，实现了N-保护的α-氨基酸和酯的室温自由基脱羧烯丙基化反应，从而得到高烯丙基胺。机理研究表明，由脱羧反应形成的α-氨基自由基的稳定性决定了竞争机制之间的主要反应途径。
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本文引用的文献
1
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Chem Sci. 2015 Jan 1;6(1):537-541. doi: 10.1039/c4sc03064h. Epub 2014 Oct 20.
2
Nickel-catalyzed cross-coupling of photoredox-generated radicals: uncovering a general manifold for stereoconvergence in nickel-catalyzed cross-couplings.镍催化的光氧化还原产生的自由基交叉偶联：揭示镍催化交叉偶联中立体收敛的一般机理。
J Am Chem Soc. 2015 Apr 22;137(15):4896-9. doi: 10.1021/ja513079r. Epub 2015 Apr 8.
3
Single-electron transmetalation: an enabling technology for secondary alkylboron cross-coupling.单电子金属转移：二级烷基硼交叉偶联的一项赋能技术。
J Am Chem Soc. 2015 Feb 18;137(6):2195-8. doi: 10.1021/ja512946e. Epub 2015 Feb 4.
4
Merging photoredox and nickel catalysis: decarboxylative cross-coupling of carboxylic acids with vinyl halides.光氧化还原与镍催化的结合：羧酸与卤代乙烯的脱羧交叉偶联反应
J Am Chem Soc. 2015 Jan 21;137(2):624-7. doi: 10.1021/ja511913h. Epub 2015 Jan 12.
5
Redox-neutral α-allylation of amines by combining palladium catalysis and visible-light photoredox catalysis.通过钯催化和可见光光氧化还原催化相结合实现胺的氧化还原中性 α-烯丙基化反应。
Angew Chem Int Ed Engl. 2015 Jan 26;54(5):1625-8. doi: 10.1002/anie.201409999. Epub 2014 Dec 10.
6
Oxidative photoredox-catalytic activation of aliphatic nucleophiles for C(sp(3))-C(sp(2)) cross-coupling reactions.氧化光氧化催化激活脂肪族亲核试剂用于 C(sp(3))-C(sp(2)) 交叉偶联反应。
Angew Chem Int Ed Engl. 2014 Dec 1;53(49):13326-8. doi: 10.1002/anie.201408748. Epub 2014 Oct 16.
7
Decarboxylative allylation of amino alkanoic acids and esters via dual catalysis.通过双催化实现氨基链烷酸和酯的脱羧烯丙基化反应。
J Am Chem Soc. 2014 Oct 1;136(39):13606-9. doi: 10.1021/ja508317j. Epub 2014 Sep 22.
8
Dual catalysis. Merging photoredox with nickel catalysis: coupling of α-carboxyl sp³-carbons with aryl halides.双催化。光氧化还原与镍催化的融合：α-羧基sp³碳与芳基卤化物的偶联。
Science. 2014 Jul 25;345(6195):437-40. doi: 10.1126/science.1255525. Epub 2014 Jun 5.
9
Dual catalysis. Single-electron transmetalation in organoboron cross-coupling by photoredox/nickel dual catalysis.双催化。通过光氧化还原/镍双催化实现有机硼交叉偶联中的单电子转金属化。
Science. 2014 Jul 25;345(6195):433-6. doi: 10.1126/science.1253647. Epub 2014 Jun 5.
10
Dual visible light photoredox and gold-catalyzed arylative ring expansion.双可见光光氧化还原与金催化的芳基化扩环反应
J Am Chem Soc. 2014 Apr 23;136(16):5844-7. doi: 10.1021/ja500716j. Epub 2014 Apr 14.
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