配体控制的钯催化的烯丙基硼酸酯和芳基卤化物的区域选择性铃木-宫浦交叉偶联反应。
Ligand-controlled palladium-catalyzed regiodivergent Suzuki-Miyaura cross-coupling of allylboronates and aryl halides.
机构信息
Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, USA.
出版信息
J Am Chem Soc. 2013 Jul 24;135(29):10642-5. doi: 10.1021/ja405950c. Epub 2013 Jul 12.
Abstract
An orthogonal set of catalyst systems has been developed for the Suzuki-Miyaura coupling of 3,3-disubstituted and 3-monosubstituted allylboronates with (hetero)aryl halides. These methods allow for the highly selective preparation of either the α- or the γ-isomeric coupling product.
摘要
已开发出一组正交的催化剂体系，用于 3,3-二取代和 3-单取代烯丙基硼酸酯与（杂）芳基卤化物的铃木-宫浦偶联反应。这些方法允许高度选择性地制备α-或γ-异构体偶联产物。
相似文献
1
Ligand-controlled palladium-catalyzed regiodivergent Suzuki-Miyaura cross-coupling of allylboronates and aryl halides.配体控制的钯催化的烯丙基硼酸酯和芳基卤化物的区域选择性铃木-宫浦交叉偶联反应。
J Am Chem Soc. 2013 Jul 24;135(29):10642-5. doi: 10.1021/ja405950c. Epub 2013 Jul 12.
2
Palladium-catalyzed Suzuki-Miyaura coupling of pyridyl-2-boronic esters with aryl halides using highly active and air-stable phosphine chloride and oxide ligands.使用高活性且对空气稳定的氯化膦和氧化膦配体，实现钯催化的吡啶 - 2 - 硼酸酯与芳基卤化物的铃木 - 宫浦偶联反应。
Org Lett. 2009 Jan 15;11(2):381-4. doi: 10.1021/ol802642g.
3
Palladium-catalyzed cross-coupling reactions of aryl boronic acids with aryl halides in water.钯催化芳基硼酸与芳基卤化物在水中的交叉偶联反应。
J Environ Sci (China). 2009;21 Suppl 1:S124-6. doi: 10.1016/S1001-0742(09)60054-1.
4
Efficient synthesis of sterically hindered arenes bearing acyclic secondary alkyl groups by Suzuki-Miyaura cross-couplings.通过 Suzuki-Miyaura 交叉偶联反应高效合成具有非环仲烷基取代基的空间位阻芳烃。
Angew Chem Int Ed Engl. 2015 Mar 16;54(12):3792-6. doi: 10.1002/anie.201411518. Epub 2015 Jan 28.
5
Rapid room temperature Buchwald-Hartwig and Suzuki-Miyaura couplings of heteroaromatic compounds employing low catalyst loadings.使用低催化剂负载量在室温下快速进行杂芳族化合物的布赫瓦尔德-哈特维希反应和铃木-宫浦反应。
Chemistry. 2006 Jun 23;12(19):5142-8. doi: 10.1002/chem.200600283.
6
Suzuki-Miyaura cross-coupling of heteroaryl halides and arylboronic acids in continuous flow.杂芳基卤化物和芳基硼酸的铃木-宫浦交叉偶联反应在连续流中进行。
Org Lett. 2011 Oct 7;13(19):5180-3. doi: 10.1021/ol202052q. Epub 2011 Sep 7.
7
Suzuki-Miyaura cross-couplings of secondary allylic boronic esters.铃木-宫浦交叉偶联反应的二级烯丙基硼酸酯。
Chem Commun (Camb). 2012 Jan 30;48(9):1230-2. doi: 10.1039/c2cc16076e. Epub 2011 Dec 19.
8
An expeditious aqueous Suzuki-Miyaura method for the substituted aryl heterocyclics.一种用于取代芳基杂环化合物的快速水相铃木-宫浦方法。
J Environ Sci (China). 2009;21 Suppl 1:S65-8. doi: 10.1016/S1001-0742(09)60039-5.
9
Diastereocontrol in asymmetric allyl-allyl cross-coupling: stereocontrolled reaction of prochiral allylboronates with prochiral allyl chlorides.非对映选择性控制的烯丙基-烯丙基交叉偶联：前手性烯丙基硼酸酯与前手性烯丙基氯化物的立体控制反应。
J Am Chem Soc. 2011 Oct 26;133(42):16778-81. doi: 10.1021/ja2075967. Epub 2011 Oct 5.
10
Highly efficient monophosphine-based catalyst for the palladium-catalyzed suzuki-miyaura reaction of heteroaryl halides and heteroaryl boronic acids and esters.用于钯催化杂芳基卤化物与杂芳基硼酸及酯的铃木-宫浦反应的高效单膦基催化剂。
J Am Chem Soc. 2007 Mar 21;129(11):3358-66. doi: 10.1021/ja068577p. Epub 2007 Feb 28.
引用本文的文献
1
Chemoenzymatic Total Synthesis of Lansai B.榄色霉素B的化学酶法全合成
Chemistry. 2025 May 8;31(26):e202500740. doi: 10.1002/chem.202500740. Epub 2025 Apr 16.
2
Stereoselective Copper-Catalyzed Cross-Coupling of α-CF-Allylboronic Acids with Diazoketones.α-三氟甲基烯丙基硼酸与重氮酮的立体选择性铜催化交叉偶联反应
J Org Chem. 2025 Feb 14;90(6):2542-2546. doi: 10.1021/acs.joc.4c02869. Epub 2025 Jan 30.
3
Copper catalyzed benzylic sp C-H alkenylation.铜催化的苄基sp C-H烯基化反应。
Chem Sci. 2024 Sep 19;15(42):17685-90. doi: 10.1039/d4sc03430a.
4
Switching Selectivity in Borylative Allyl-Allyl Cross-Coupling through Synergistic Catalysis.通过协同催化实现硼氢化烯丙基-烯丙基交叉偶联中的选择性切换
J Am Chem Soc. 2024 Aug 7;146(31):21977-21988. doi: 10.1021/jacs.4c07188. Epub 2024 Jul 24.
5
Nucleophilic aromatization of monoterpenes from isoprene under nickel/iodine cascade catalysis.在镍/碘级联催化下异戊二烯单萜的亲核芳构化反应
Nat Commun. 2023 Nov 4;14(1):7087. doi: 10.1038/s41467-023-42847-6.
6
Synthesis of Quaternary and Tertiary Carbon-Substituted Arenes by Lewis Base Promoted Site-Selective Coupling with Allylic Nucleophiles.通过路易斯碱促进的与烯丙基亲核试剂的位点选择性偶联合成季碳和叔碳取代芳烃。
Angew Chem Int Ed Engl. 2023 Aug 21;62(34):e202306277. doi: 10.1002/anie.202306277. Epub 2023 Jul 11.
7
Palladium-Catalyzed Synthesis of 1-Alkylidene-2-dialkylaminomethyl Cyclobutane Derivatives via Pd-Catalyzed Alkene Difunctionalization Reactions: Influence of Nucleophile and Water on the Reaction Mechanism.钯催化烯丙基二烷基甲胺基环丁烷衍生物的合成：通过 Pd 催化的烯烃双官能化反应：亲核试剂和水对反应机理的影响。
Org Lett. 2023 May 12;25(18):3245-3248. doi: 10.1021/acs.orglett.3c00954. Epub 2023 May 1.
8
Cooperative Pd/Cu Catalysis for Alkene Arylboration: Opportunities for Divergent Reactivity.用于烯烃芳基硼化的协同钯/铜催化：不同反应性的机遇
ACS Catal. 2022 Feb 4;12(3):2058-2063. doi: 10.1021/acscatal.1c05696. Epub 2022 Jan 24.
9
Sulfenofunctionalization of Chiral α-Trifluoromethyl Allylboronic Acids: Asymmetric Synthesis of SCF , SCF R, SCN and SAr Compounds.手性α-三氟甲基烯丙基硼酸的亚磺酰官能化：SCF、SCF R、SCN和SAr化合物的不对称合成
Angew Chem Int Ed Engl. 2022 Nov 14;61(46):e202210509. doi: 10.1002/anie.202210509. Epub 2022 Oct 17.
10
A General Strategy for the Asymmetric Preparation of α-Stereogenic Allyl Silanes, Germanes, and Boronate Esters via Dual Copper Hydride- and Palladium-Catalysis.通过双铜氢化物和钯催化作用，实现α-手性烯丙基硅烷、锗烷和硼酸酯的不对称制备的通用策略。
Angew Chem Int Ed Engl. 2022 Nov 21;61(47):e202212630. doi: 10.1002/anie.202212630. Epub 2022 Oct 18.
本文引用的文献
1
Palladium-catalyzed synthesis and isolation of functionalized allylboronic acids: selective, direct allylboration of ketones.钯催化合成和官能化烯丙基硼酸的分离：酮的选择性、直接烯丙基硼化。
Angew Chem Int Ed Engl. 2012 Dec 21;51(52):13050-3. doi: 10.1002/anie.201207951. Epub 2012 Nov 19.
2
Regioselective cross-coupling of allylboronic acid pinacol ester derivatives with aryl halides via Pd-PEPPSI-IPent.钯-PEPPSI-IPent 促进烯丙基硼酸频哪醇酯衍生物与芳基卤化物的区域选择性交叉偶联。
J Am Chem Soc. 2012 Oct 24;134(42):17470-3. doi: 10.1021/ja308613b. Epub 2012 Oct 15.
3
Dialkylbiaryl Phosphines in Pd-Catalyzed Amination: A User's Guide.钯催化胺化反应中的二烷基联芳基膦：用户指南
Chem Sci. 2011;2(1):27-50. doi: 10.1039/C0SC00331J.
4
Ni- and Pd-catalyzed synthesis of substituted and functionalized allylic boronates.镍和钯催化的取代和官能化烯丙基硼酸酯的合成。
Org Lett. 2012 Mar 16;14(6):1416-9. doi: 10.1021/ol3001552. Epub 2012 Feb 29.
5
Suzuki-Miyaura cross-couplings of secondary allylic boronic esters.铃木-宫浦交叉偶联反应的二级烯丙基硼酸酯。
Chem Commun (Camb). 2012 Jan 30;48(9):1230-2. doi: 10.1039/c2cc16076e. Epub 2011 Dec 19.
6
Hydride as a leaving group in the reaction of pinacolborane with halides under ambient Grignard and Barbier conditions. One-pot synthesis of alkyl, aryl, heteroaryl, vinyl, and allyl pinacolboronic esters.在环境格氏和巴尔比耶条件下，氢化物作为频哪醇硼烷与卤化物反应的离去基团。一锅法合成烷基、芳基、杂芳基、乙烯基和烯丙基频哪醇硼酸酯。
J Org Chem. 2011 Dec 2;76(23):9602-10. doi: 10.1021/jo201093u. Epub 2011 Nov 1.
7
Indole prenylation in alkaloid synthesis.生物碱合成中的吲哚异戊烯基化作用。
Top Curr Chem. 2012;309:67-129. doi: 10.1007/128_2011_204.
8
Concise total syntheses of variecolortides A and B through an unusual hetero-Diels-Alder reaction.通过一种不寻常的杂环狄尔斯-阿尔德反应对变色肽A和B进行简洁的全合成。
Angew Chem Int Ed Engl. 2011 Feb 7;50(6):1402-5. doi: 10.1002/anie.201006154. Epub 2010 Dec 29.
9
A new palladium precatalyst allows for the fast Suzuki-Miyaura coupling reactions of unstable polyfluorophenyl and 2-heteroaryl boronic acids.一种新型钯前催化剂可实现不稳定的多氟代苯基和 2-杂芳基硼酸的快速铃木-宫浦偶联反应。
J Am Chem Soc. 2010 Oct 13;132(40):14073-5. doi: 10.1021/ja1073799.
10
On the stereochemical course of palladium-catalyzed cross-coupling of allylic silanolate salts with aromatic bromides.钯催化烯丙基硅醇盐与芳基溴化物交叉偶联反应的立体化学过程
J Am Chem Soc. 2010 Mar 17;132(10):3612-20. doi: 10.1021/ja910804u.
Zotero 插件