硅胶负载的低聚苄基磷酸酯（Si-OBP）和三唑磷酸酯（Si-OTP）烷基化试剂。
Silica-Supported Oligomeric Benzyl Phosphate (Si-OBP) and Triazole Phosphate (Si-OTP) Alkylating Reagents.
作者信息
Maity Pradip K, Faisal Saqib, Rolfe Alan, Stoianova Diana, Hanson Paul R
机构信息
Department of Chemistry, University of Kansas , 1251 Wescoe Hall Drive, Lawrence, Kansas 66045-7582, United States.
The University of Kansas Center for Chemical Methodologies and Library Development (KU-CMLD) , 2034-Becker Drive, Delbert M. Shankel Structural Biology Center, Lawrence, Kansas 66047, United States.
出版信息
J Org Chem. 2015 Oct 16;80(20):9942-50. doi: 10.1021/acs.joc.5b01456. Epub 2015 Oct 2.
Abstract
The syntheses of silica-supported oligomeric benzyl phosphates (Si-OBP(n)) and triazole phosphates (Si-OTP(n)) using ring-opening metathesis polymerization (ROMP) for use as efficient alkylating reagents is reported. Ease of synthesis and grafting onto the surface of norbornenyl-tagged (Nb-tagged) silica particles has been demonstrated for benzyl phosphate and triazole phosphate monomers. It is shown that these silica polymer hybrid reagents, Si-OBP(n) and Si-OTP(n), can be used to carry out alkylation reactions with an array of different nucleophiles to afford the corresponding benzylated and (triazolyl)methylated products in good yield and high purity.
摘要
报道了使用开环易位聚合（ROMP）合成二氧化硅负载的低聚苄基磷酸酯（Si-OBP(n)）和三唑基磷酸酯（Si-OTP(n)），用作高效烷基化试剂。苄基磷酸酯和三唑基磷酸酯单体已证明易于合成并接枝到降冰片烯基标记（Nb标记）的二氧化硅颗粒表面。结果表明，这些二氧化硅聚合物杂化试剂Si-OBP(n)和Si-OTP(n)可用于与一系列不同亲核试剂进行烷基化反应，以高收率和高纯度得到相应的苄基化和（三唑基）甲基化产物。
相似文献
1
Silica-Supported Oligomeric Benzyl Phosphate (Si-OBP) and Triazole Phosphate (Si-OTP) Alkylating Reagents.硅胶负载的低聚苄基磷酸酯（Si-OBP）和三唑磷酸酯（Si-OTP）烷基化试剂。
J Org Chem. 2015 Oct 16;80(20):9942-50. doi: 10.1021/acs.joc.5b01456. Epub 2015 Oct 2.
2
Synthesis of High-Load, Hybrid Silica-Immobilized Heterocyclic Benzyl Phosphate (Si-OHBP) and Triazolyl Phosphate (Si-OHTP) Alkylating Reagents.高负载量的杂化二氧化硅固定化杂环苄基磷酸酯（Si-OHBP）和磷酸三唑酯（Si-OHTP）烷基化试剂的合成。
ACS Comb Sci. 2016 Jul 11;18(7):394-8. doi: 10.1021/acscombsci.6b00042. Epub 2016 Jun 14.
3
Application of Silica-Supported Alkylating Reagents in a One-Pot, Sequential Protocol to Diverse Benzoxathiazepine 1,1-Dioxides.硅胶负载的烷基化试剂在一锅法连续合成多种苯并[1,4]噻嗪-1,1-二氧化物中的应用。
ACS Comb Sci. 2016 Jul 11;18(7):387-93. doi: 10.1021/acscombsci.6b00041. Epub 2016 Jun 14.
4
"Click"-capture, ring-opening metathesis polymerization (ROMP), release: facile triazolation utilizing ROMP-derived oligomeric phosphates.点击捕获、开环易位聚合 (ROMP)、释放：利用 ROMP 衍生的低聚磷酸酯的简便三唑化。
Org Lett. 2011 Apr 15;13(8):2038-41. doi: 10.1021/ol200430c. Epub 2011 Mar 24.
5
ROMP-derived oligomeric phosphates for application in facile benzylation.ROMP 衍生的低聚物磷酸酯在简便的苄基化反应中的应用。
Org Lett. 2010 Jul 2;12(13):2904-7. doi: 10.1021/ol1006604.
6
High-load, hybrid Si-ROMP reagents.高负荷、混合 Si-ROMP 试剂。
Org Lett. 2011 Jan 7;13(1):4-7. doi: 10.1021/ol102239h. Epub 2010 Dec 1.
7
Facile (triazolyl)methylation of MACOS-derived benzofused sultams utilizing ROMP-derived OTP reagents.利用 ROMP 衍生的 OTP 试剂对 MACOS 衍生的苯并稠合磺酰胺进行易（三唑基）甲基化。
ACS Comb Sci. 2012 Apr 9;14(4):268-72. doi: 10.1021/co2001839. Epub 2012 Mar 5.
8
Amino benzoic acid modified silica--an improved catalyst for the mono-substituted product in the benzylation of toluene with benzyl chloride.氨基苯甲酸改性硅胶——甲苯与苄基氯苄基化反应中制备单取代产物的一种改进型催化剂。
J Colloid Interface Sci. 2007 Jul 1;311(1):135-43. doi: 10.1016/j.jcis.2007.02.083. Epub 2007 Mar 3.
9
Solvent-free synthesis of silicoaluminophosphate zeolites.硅铝磷酸盐沸石的无溶剂合成
Angew Chem Int Ed Engl. 2013 Aug 26;52(35):9172-5. doi: 10.1002/anie.201302672. Epub 2013 Jul 10.
10
Synthesis and photochromism of tungstophosphate-functionalized ordered mesoporous hybrid silica.钨磷酸盐功能化有序介孔杂化二氧化硅的合成与光致变色
J Nanosci Nanotechnol. 2011 Mar;11(3):2349-53. doi: 10.1166/jnn.2011.3127.
引用本文的文献
1
Development and Application of a Recyclable High-Load Magnetic Co/C Hybrid ROMP-Derived Benzenesulfonyl Chloride Reagent and Utility of Corresponding Analogues.一种可回收的高负载磁性 Co/C 杂化 ROMP 衍生苯磺酰氯试剂的开发与应用及相应类似物的应用。
Org Lett. 2017 May 5;19(9):2274-2277. doi: 10.1021/acs.orglett.7b00792. Epub 2017 Apr 24.
2
Synthesis of High-Load, Hybrid Silica-Immobilized Heterocyclic Benzyl Phosphate (Si-OHBP) and Triazolyl Phosphate (Si-OHTP) Alkylating Reagents.高负载量的杂化二氧化硅固定化杂环苄基磷酸酯（Si-OHBP）和磷酸三唑酯（Si-OHTP）烷基化试剂的合成。
ACS Comb Sci. 2016 Jul 11;18(7):394-8. doi: 10.1021/acscombsci.6b00042. Epub 2016 Jun 14.
3
Application of Silica-Supported Alkylating Reagents in a One-Pot, Sequential Protocol to Diverse Benzoxathiazepine 1,1-Dioxides.硅胶负载的烷基化试剂在一锅法连续合成多种苯并[1,4]噻嗪-1,1-二氧化物中的应用。
ACS Comb Sci. 2016 Jul 11;18(7):387-93. doi: 10.1021/acscombsci.6b00041. Epub 2016 Jun 14.
本文引用的文献
1
Surface functionalization of silica by Si-H activation of hydrosilanes.硅氢烷的 Si-H 活化对二氧化硅进行表面功能化。
J Am Chem Soc. 2014 Aug 20;136(33):11570-3. doi: 10.1021/ja504115d. Epub 2014 Aug 7.
2
MCF-supported boronic acids as efficient catalysts for direct amide condensation of carboxylic acids and amines.MCF负载的硼酸作为羧酸和胺直接酰胺缩合反应的高效催化剂。
Chem Commun (Camb). 2014 Jul 7;50(53):7017-9. doi: 10.1039/c4cc01148a. Epub 2014 May 21.
3
Tripod immobilization of triphenylphosphane on a silica-gel surface to enable selective mono-ligation to palladium: application to Suzuki-Miyaura cross-coupling reactions with chloroarenes.三苯基膦在硅胶表面的三脚固定化，以实现对钯的选择性单配位：在氯代芳烃的 Suzuki-Miyaura 交叉偶联反应中的应用。
Chemistry. 2014 Jan 20;20(4):1057-65. doi: 10.1002/chem.201304081. Epub 2013 Dec 20.
4
Silica-immobilized chiral dirhodium(II) catalyst for enantioselective carbenoid reactions.用于对映选择性碳烯反应的硅烷化手性二钌(II)催化剂。
Org Lett. 2013 Dec 20;15(24):6136-9. doi: 10.1021/ol403006r. Epub 2013 Nov 19.
5
Synthesis and library construction of privileged tetra-substituted Δ5-2-oxopiperazine as β-turn structure mimetics.作为β-转角结构类似物的特权四取代Δ5-2-氧代哌嗪的合成和库构建。
ACS Comb Sci. 2014 Jan 13;16(1):24-32. doi: 10.1021/co400128a. Epub 2013 Nov 26.
6
Removal of ruthenium using a silica gel supported reagent.使用硅胶负载试剂去除钌。
Org Lett. 2013 Nov 1;15(21):5416-9. doi: 10.1021/ol402339e. Epub 2013 Oct 15.
7
Copper-catalyzed electrophilic amination of organolithiums mediated by recoverable siloxane transfer agents.铜催化的有机锂试剂的亲电胺化反应，由可回收的硅氧烷转移试剂介导。
Org Lett. 2013 Sep 20;15(18):4872-5. doi: 10.1021/ol4023084. Epub 2013 Sep 3.
8
Cell-based medicinal chemistry optimization of high-throughput screening (HTS) hits for orally active antimalarials. Part 1: challenges in potency and absorption, distribution, metabolism, excretion/pharmacokinetics (ADME/PK).基于细胞的药物化学优化高通量筛选 (HTS) 命中物，用于口服抗疟药物。第 1 部分：效力和吸收、分布、代谢、排泄/药代动力学 (ADME/PK) 中的挑战。
J Med Chem. 2013 Oct 24;56(20):7741-9. doi: 10.1021/jm400314m. Epub 2013 Sep 13.
9
Polymer-supported siloxane transfer agents for Pd-catalyzed cross-coupling reactions.聚合物负载的硅氧烷转移试剂在 Pd 催化的交叉偶联反应中的应用。
Org Lett. 2013 Aug 16;15(16):4258-61. doi: 10.1021/ol402047d. Epub 2013 Jul 31.
10
Ring-opening metathesis polymerization-based recyclable magnetic acylation reagents.基于开环易位聚合的可回收磁性酰化试剂。
ChemSusChem. 2013 Apr;6(4):721-9. doi: 10.1002/cssc.201200453. Epub 2013 Feb 20.
Zotero 插件