钯催化的丁二烯 1,4-双官能化反应形成缺碳多烯。
Palladium-catalyzed 1,4-difunctionalization of butadiene to form skipped polyenes.
机构信息
Department of Chemistry, University of Utah, 315 South 1400 East, Salt Lake City, Utah 84112, USA.
出版信息
J Am Chem Soc. 2013 Mar 20;135(11):4167-70. doi: 10.1021/ja3110544. Epub 2013 Mar 12.
Abstract
A palladium-catalyzed 1,4-addition across the commodity chemical 1,3-butadiene to afford skipped polyene products is reported. Through a palladium σ → π → σ allyl isomerization, two new carbon-carbon bonds are formed with high regioselectivity and trans stereoselectivity of the newly formed alkene. The utility of this method is highlighted by the successful synthesis of the ripostatin A skipped triene core.
摘要
报道了一种钯催化的 1,4-加成反应，使商品化学物质 1,3-丁二烯发生反应，生成缺电子多烯产物。通过钯的 σ → π → σ 烯丙基异构化，以高区域选择性和新形成的烯烃的反式立体选择性形成两个新的碳-碳键。该方法的实用性通过成功合成 ripostatin A 缺电子三烯核心得到了突出体现。
相似文献
1
Palladium-catalyzed 1,4-difunctionalization of butadiene to form skipped polyenes.钯催化的丁二烯 1,4-双官能化反应形成缺碳多烯。
J Am Chem Soc. 2013 Mar 20;135(11):4167-70. doi: 10.1021/ja3110544. Epub 2013 Mar 12.
2
Access to skipped polyene macrolides through ring-closing metathesis: total synthesis of the RNA polymerase inhibitor ripostatin B.通过闭环复分解反应获得被跳过的多烯大环内酯：RNA 聚合酶抑制剂利帕他汀 B 的全合成。
Angew Chem Int Ed Engl. 2012 Apr 2;51(14):3396-400. doi: 10.1002/anie.201108692. Epub 2012 Feb 15.
3
Total synthesis of RNA-polymerase inhibitor ripostatin B and 15-deoxyripostatin A.RNA 聚合酶抑制剂利波他汀 B 和 15-脱氧利波他汀 A 的全合成。
Angew Chem Int Ed Engl. 2012 Apr 2;51(14):3401-4. doi: 10.1002/anie.201108749. Epub 2012 Feb 29.
4
Stereoconvergent palladium-catalyzed carbonylation of both E and Z isomers of a 2-trifloxy-1,3-butadiene.2-三氟氧基-1,3-丁二烯的E型和Z型异构体的立体收敛钯催化羰基化反应
Org Lett. 2000 Sep 7;2(18):2905-7. doi: 10.1021/ol0063609.
5
Tandem Stille/Suzuki-Miyaura coupling of a hetero-bis-metalated diene. Rapid, one-pot assembly of polyene systems.杂双金属化二烯的串联Stille/Suzuki-Miyaura偶联反应。多烯体系的快速一锅法组装。
Org Lett. 2005 May 26;7(11):2289-91. doi: 10.1021/ol050768u.
6
Enantioselective desymmetrizing palladium catalyzed carbonylation reactions: the catalytic asymmetric synthesis of quaternary carbon center containing 1,3-dienes.对映选择性去对称钯催化羰基化反应：含季碳中心的 1,3-二烯的催化不对称合成。
Org Biomol Chem. 2010 Feb 21;8(4):758-60. doi: 10.1039/b923186b. Epub 2009 Dec 21.
7
Synthesis of highly substituted 1,3-butadienes by palladium-catalyzed arylation of internal alkynes.通过钯催化内炔烃的芳基化反应合成高度取代的1,3 - 丁二烯
Angew Chem Int Ed Engl. 2004 Sep 27;43(38):5063-5. doi: 10.1002/anie.200460409.
8
Catalyst-controlled regioselectivity in the synthesis of branched conjugated dienes via aerobic oxidative Heck reactions.通过有氧氧化 Heck 反应合成支化共轭二烯中的催化剂控制区域选择性。
J Am Chem Soc. 2012 Oct 10;134(40):16496-9. doi: 10.1021/ja307371w. Epub 2012 Sep 28.
9
Total synthesis of ripostatin A.利波他汀 A 的全合成。
Org Lett. 2012 Sep 7;14(17):4690-3. doi: 10.1021/ol302219x. Epub 2012 Aug 23.
10
Highly Regio- and Stereoselective Catalytic Synthesis of Conjugated Dienes and Polyenes.高区域和立体选择性催化合成共轭二烯和多烯。
J Am Chem Soc. 2018 Jul 11;140(27):8434-8438. doi: 10.1021/jacs.8b05421. Epub 2018 Jun 26.
引用本文的文献
1
Observation of unusual outer-sphere mechanism using simple alkenes as nucleophiles in allylation chemistry.在烯丙基化化学中使用简单烯烃作为亲核试剂对异常外层机理的观察。
Nat Commun. 2024 May 21;15(1):4317. doi: 10.1038/s41467-024-48541-5.
2
Palladium-Catalyzed Regiodivergent Three-Component Alkenylamination of 1,3-Dienes with Alkyl and Aryl Amines.钯催化的1,3-二烯与烷基和芳基胺的区域发散性三组分烯基胺化反应
J Am Chem Soc. 2023 Dec 20;145(50):27680-27689. doi: 10.1021/jacs.3c09873. Epub 2023 Dec 6.
3
Mechanistic study on the side arm effect in a palladium/Xu-Phos-catalyzed enantioselective alkoxyalkenylation of γ-hydroxyalkenes.钯/徐氏膦催化γ-羟基烯烃对映选择性烷氧基烯基化反应中侧臂效应的机理研究
Nat Commun. 2023 Nov 22;14(1):7611. doi: 10.1038/s41467-023-43202-5.
4
Divergent 1,2-carboallylation of terminal alkynes enabled by metallaphotoredox catalysis with switchable triplet energy transfer.通过具有可切换三重态能量转移的金属光氧化还原催化实现末端炔烃的发散性1,2-碳烯基化反应
Chem Sci. 2023 Oct 13;14(43):12143-12151. doi: 10.1039/d3sc04645a. eCollection 2023 Nov 8.
5
Copper-Catalyzed Asymmetric Acylboration of 1,3-Butadienylboronate with Acyl Fluorides.铜催化1,3 - 丁二烯硼酸酯与酰氟的不对称酰基硼化反应
Angew Chem Int Ed Engl. 2023 Oct 23;62(43):e202304796. doi: 10.1002/anie.202304796. Epub 2023 Sep 15.
6
Serendipitous synthesis of cross-conjugated dienes by cascade deconstructive esterification of thiomorpholinone-tethered alkenoic acids.通过硫代吗啉酮连接的链烯酸的级联解构酯化反应意外合成交叉共轭二烯。
RSC Adv. 2023 Jan 23;13(5):3181-3185. doi: 10.1039/d2ra07916j. eCollection 2023 Jan 18.
7
Cobalt-catalyzed branched selective hydroallylation of terminal alkynes.钴催化末端炔烃的支链选择性氢烯基化反应。
Nat Commun. 2022 Aug 3;13(1):4518. doi: 10.1038/s41467-022-32291-3.
8
Ruthenium-catalyzed formal sp C-H activation of allylsilanes/esters with olefins: efficient access to functionalized 1,3-dienes.钌催化烯丙基硅烷/酯与烯烃的形式sp C-H活化：高效合成官能化1,3-二烯
Chem Sci. 2021 Feb 2;12(12):4367-4372. doi: 10.1039/d0sc06845d.
9
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.
10
Reactivity of Stabilized Vinyldiazo Compounds toward Alkenyl- and Alkynylsilanes under Gold Catalysis: Regio- and Stereoselective Synthesis of Skipped Dienes and Enynes.金催化下稳定的乙烯基重氮化合物对烯基硅烷和炔基硅烷的反应活性：跳烯和烯炔的区域和立体选择性合成
Org Lett. 2021 Jun 4;23(11):4452-4456. doi: 10.1021/acs.orglett.1c01381. Epub 2021 May 13.
本文引用的文献
1
Total synthesis of ripostatin A.利波他汀 A 的全合成。
Org Lett. 2012 Sep 7;14(17):4690-3. doi: 10.1021/ol302219x. Epub 2012 Aug 23.
2
Palladium-catalyzed 1,1-difunctionalization of ethylene.钯催化的乙烯 1,1-双官能化反应。
J Am Chem Soc. 2012 Jul 18;134(28):11372-5. doi: 10.1021/ja304344h. Epub 2012 Jul 10.
3
Palladium-catalyzed allylic cross-coupling reactions of primary and secondary homoallylic electrophiles.钯催化的伯、仲同烯丙基亲电试剂的烯丙基交叉偶联反应。
J Am Chem Soc. 2012 Jul 18;134(28):11408-11. doi: 10.1021/ja305403s. Epub 2012 Jul 6.
4
Enantioselective C-H crotylation of primary alcohols via hydrohydroxyalkylation of butadiene.通过丁二烯的氢羟烷基化反应实现伯醇的对映选择性 C-H 丙烯基化。
Science. 2012 Apr 20;336(6079):324-7. doi: 10.1126/science.1219274. Epub 2012 Mar 22.
5
Total synthesis of RNA-polymerase inhibitor ripostatin B and 15-deoxyripostatin A.RNA 聚合酶抑制剂利波他汀 B 和 15-脱氧利波他汀 A 的全合成。
Angew Chem Int Ed Engl. 2012 Apr 2;51(14):3401-4. doi: 10.1002/anie.201108749. Epub 2012 Feb 29.
6
Access to skipped polyene macrolides through ring-closing metathesis: total synthesis of the RNA polymerase inhibitor ripostatin B.通过闭环复分解反应获得被跳过的多烯大环内酯：RNA 聚合酶抑制剂利帕他汀 B 的全合成。
Angew Chem Int Ed Engl. 2012 Apr 2;51(14):3396-400. doi: 10.1002/anie.201108692. Epub 2012 Feb 15.
7
Continuous photochemical generation of catalytically active [CpRu]+ complexes from CpRu(η6-C6H6)PF6.连续光化学法从 CpRu(η6-C6H6)PF6 生成催化活性的 [CpRu]+ 配合物。
Org Lett. 2011 Dec 16;13(24):6414-7. doi: 10.1021/ol2027015. Epub 2011 Nov 15.
8
Gaining absolute control of the regiochemistry in the cobalt-catalyzed 1,4-hydrovinylation reaction.在钴催化的 1,4-氢甲酰化反应中获得区域化学的绝对控制。
Org Lett. 2011 Dec 2;13(23):6236-9. doi: 10.1021/ol202696n. Epub 2011 Oct 31.
9
Iridium-catalyzed allylic vinylation and asymmetric allylic amination reactions with o-aminostyrenes.铱催化的烯丙基乙烯基化和不对称烯丙基氨化反应与邻氨基苯乙烯。
J Am Chem Soc. 2011 Nov 23;133(46):19006-14. doi: 10.1021/ja2092954. Epub 2011 Nov 2.
10
Gram-scale synthesis of iejimalide B.大规模合成 iejimalide B。
Chemistry. 2011 Jun 14;17(25):6964-72. doi: 10.1002/chem.201100178. Epub 2011 May 9.
Zotero 插件