2,6-双（吡唑-1-基）吡啶（1-bpp）作为烷基吡啶盐Negishi烷基化反应的通用配体。
2,6-Bis(pyrazol-1-yl)pyridine (1-bpp) as a General Ligand for the Negishi Alkylation of Alkylpyridinium Salts.
作者信息
Baker Kristen M, Bercher Olivia P, Twitty J Cameron, Mortimer Thomas, Watson Mary P
机构信息
Department of Chemistry & Biochemistry, University of Delaware, Newark, Delaware 19716, United States.
出版信息
J Org Chem. 2024 Nov 15;89(22):16249-16252. doi: 10.1021/acs.joc.3c00665. Epub 2023 Jun 27.
Abstract
A Ni/1-bpp catalyst was demonstrated to be effective in the Negishi alkylation with multiple classes of alkylpyridinium salts, including α-primary and α-secondary. These conditions are also effective for benzylic pyridinium salts, demonstrating the successful Negishi alkylation of benzylic pyridinium salts for the first time. Further, 14 derivatives of 1-bpp were prepared with a variety of steric and electronic properties to study how these changes impact the success of the Negishi alkylation.
摘要
已证明镍/1-联吡啶催化剂在与多类烷基吡啶盐（包括α-伯烷基和α-仲烷基）的根岸烷基化反应中有效。这些条件对苄基吡啶盐也有效，首次证明了苄基吡啶盐成功进行根岸烷基化反应。此外，制备了具有各种空间和电子性质的14种1-联吡啶衍生物，以研究这些变化如何影响根岸烷基化反应的成功率。
相似文献
1
2,6-Bis(pyrazol-1-yl)pyridine (1-bpp) as a General Ligand for the Negishi Alkylation of Alkylpyridinium Salts.2,6-双（吡唑-1-基）吡啶（1-bpp）作为烷基吡啶盐Negishi烷基化反应的通用配体。
J Org Chem. 2024 Nov 15;89(22):16249-16252. doi: 10.1021/acs.joc.3c00665. Epub 2023 Jun 27.
2
Harnessing Alkylpyridinium Salts as Electrophiles in Deaminative Alkyl-Alkyl Cross-Couplings.利用烷基吡啶鎓盐作为亲电试剂进行脱氨烷基-烷基交叉偶联反应。
J Am Chem Soc. 2019 Feb 13;141(6):2257-2262. doi: 10.1021/jacs.9b00111. Epub 2019 Jan 30.
3
Beyond Spin Crossover: Optical and Electronic Horizons of 2,6-Bis(pyrazol-1-yl)pyridine Ligands and Complexes.超越自旋交叉：2,6-双（吡唑-1-基）吡啶配体与配合物的光学和电子前沿
Molecules. 2025 Mar 14;30(6):1314. doi: 10.3390/molecules30061314.
4
Extraction and complexation studies with 2,6-bis(5-(-butyl)-1-pyrazol-3-yl)pyridine in the presence of 2-bromohexanoic acid.在2-溴己酸存在下，用2,6-双(5-(正丁基)-1-吡唑-3-基)吡啶进行萃取和络合研究。
RSC Adv. 2024 Sep 5;14(39):28415-28422. doi: 10.1039/d4ra05630b. eCollection 2024 Sep 4.
5
Heteroleptic iron(II) complexes of chiral 2,6-bis(oxazolin-2-yl)-pyridine (PyBox) and 2,6-bis(thiazolin-2-yl)pyridine ligands - the interplay of two different ligands on the metal ion spin sate.手性2,6-双（恶唑啉-2-基）吡啶（PyBox）和2,6-双（噻唑啉-2-基）吡啶配体的异配体铁（II）配合物——两种不同配体对金属离子自旋态的相互作用
Dalton Trans. 2022 Mar 15;51(11):4262-4274. doi: 10.1039/d2dt00393g.
6
Above room temperature spin crossover in thioamide-functionalised 2,6-bis(pyrazol-1-yl)pyridine iron(ii) complexes.室温顺磁-自旋交叉在硫代酰胺功能化 2,6-双（吡唑-1-基）吡啶铁（II）配合物中的表现。
Dalton Trans. 2018 Dec 18;48(1):90-98. doi: 10.1039/c8dt03240h.
7
Unravelling the spin-state of solvated [Fe(bpp)] spin-crossover complexes: structure-function relationship.解析溶剂化 [Fe(bpp)] 自旋交叉配合物的自旋态：结构-功能关系。
Dalton Trans. 2018 Aug 21;47(31):10453-10462. doi: 10.1039/c8dt01269e. Epub 2018 May 23.
8
Synthesis and characterization of heptacoordinated molybdenum(II) complexes supported with 2,6-bis(pyrazol-3-yl)pyridine (bpp) ligands.
Dalton Trans. 2025 Feb 11;54(7):2860-2870. doi: 10.1039/d4dt03264k.
9
2,6-Bis(5-(2,2-dimethylpropyl)-1H-pyrazol-3-yl)pyridine as a ligand for efficient actinide(III)/lanthanide(III) separation.2,6-双(5-(2,2-二甲基丙基)-1H-吡唑-3-基)吡啶作为高效分离锕系(III)/镧系(III)元素的配体。
Inorg Chem. 2012 May 7;51(9):5199-207. doi: 10.1021/ic3000526. Epub 2012 Apr 19.
10
Towards the Molecular Design of Spin-Crossover Complexes of 2,6-Bis(pyrazol-3-yl)pyridines.迈向2,6-双（吡唑-3-基）吡啶自旋交叉配合物的分子设计
Chemistry. 2020 May 4;26(25):5629-5638. doi: 10.1002/chem.202000047. Epub 2020 Mar 12.
引用本文的文献
1
Beyond Spin Crossover: Optical and Electronic Horizons of 2,6-Bis(pyrazol-1-yl)pyridine Ligands and Complexes.超越自旋交叉：2,6-双（吡唑-1-基）吡啶配体与配合物的光学和电子前沿
Molecules. 2025 Mar 14;30(6):1314. doi: 10.3390/molecules30061314.
2
A decarbonylative approach to alkylnickel intermediates and C(sp)-C(sp) bond formation.一种生成烷基镍中间体及形成C(sp)-C(sp)键的脱羰方法。
Science. 2024 Sep 20;385(6715):1331-1337. doi: 10.1126/science.abi4860. Epub 2024 Sep 19.
本文引用的文献
1
Nickel Catalysis via S2 Homolytic Substitution: The Double Decarboxylative Cross-Coupling of Aliphatic Acids.镍催化的 S2 均裂取代反应：脂肪族酸的双脱羧交叉偶联反应。
J Am Chem Soc. 2022 Nov 23;144(46):21278-21286. doi: 10.1021/jacs.2c08989. Epub 2022 Nov 14.
2
Ni-electrocatalytic Csp-Csp doubly decarboxylative coupling.镍电催化 Csp-Csp 双重脱羧偶联。
Nature. 2022 Jun;606(7913):313-318. doi: 10.1038/s41586-022-04691-4. Epub 2022 Apr 5.
3
Dissection of Alkylpyridinium Structures to Understand Deamination Reactions.剖析烷基吡啶鎓结构以理解脱氨基反应。
ACS Catal. 2021 Jul 16;11(14):8456-8466. doi: 10.1021/acscatal.1c01860. Epub 2021 Jun 28.
4
Nickel-catalyzed three-component olefin reductive dicarbofunctionalization to access alkylborates.镍催化的三组分烯烃还原双碳官能化反应以制备硼酸烷基酯。
Chem Sci. 2020 Jul 8;11(30):7950-7956. doi: 10.1039/d0sc02054k.
5
Engaging Alkenes and Alkynes in Deaminative Alkyl-Alkyl and Alkyl-Vinyl Cross-Couplings of Alkylpyridinium Salts.参与脱氨烷基-烷基和烷基-乙烯基交叉偶联反应的烯丙基和炔烃与烷基吡啶鎓盐。
Org Lett. 2019 Dec 6;21(23):9738-9741. doi: 10.1021/acs.orglett.9b03899. Epub 2019 Nov 25.
6
Harnessing Alkylpyridinium Salts as Electrophiles in Deaminative Alkyl-Alkyl Cross-Couplings.利用烷基吡啶鎓盐作为亲电试剂进行脱氨烷基-烷基交叉偶联反应。
J Am Chem Soc. 2019 Feb 13;141(6):2257-2262. doi: 10.1021/jacs.9b00111. Epub 2019 Jan 30.
7
Mechanistic Characterization of (Xantphos)Ni(I)-Mediated Alkyl Bromide Activation: Oxidative Addition, Electron Transfer, or Halogen-Atom Abstraction.（Xantphos）Ni(I）介导的烷基溴化物活化的机理表征：氧化加成、电子转移还是卤素原子攫取。
J Am Chem Soc. 2019 Jan 30;141(4):1788-1796. doi: 10.1021/jacs.8b13499. Epub 2019 Jan 17.
8
Vinylation of Benzylic Amines via C-N Bond Functionalization of Benzylic Pyridinium Salts.通过苄基吡啶鎓盐的C-N键官能化实现苄胺的乙烯基化反应
Synthesis (Stuttg). 2018 Aug;50(16):3231-3237. doi: 10.1055/s-0037-1610084. Epub 2018 Jun 8.
9
Structural and Synthetic Insights into Pyridine Homocouplings Mediated by a β-Diketiminato Magnesium Amide Complex.β-二酮亚胺镁酰胺配合物介导的吡啶同系物偶联的结构和合成见解。
Chemistry. 2018 Oct 1;24(55):14830-14835. doi: 10.1002/chem.201803297. Epub 2018 Sep 7.
10
Transforming Benzylic Amines into Diarylmethanes: Cross-Couplings of Benzylic Pyridinium Salts via C-N Bond Activation.苄基胺转化为二芳基甲烷：通过 C-N 键活化的苄基吡啶鎓盐的交叉偶联反应。
Org Lett. 2018 May 18;20(10):3030-3033. doi: 10.1021/acs.orglett.8b01062. Epub 2018 May 10.
Zotero 插件