• 文献检索
  • 文档翻译
  • 深度研究
  • 学术资讯
  • Suppr Zotero 插件Zotero 插件
  • 邀请有礼
  • 套餐&价格
  • 历史记录
应用&插件
Suppr Zotero 插件Zotero 插件浏览器插件Mac 客户端Windows 客户端微信小程序
定价
高级版会员购买积分包购买API积分包
服务
文献检索文档翻译深度研究API 文档MCP 服务
关于我们
关于 Suppr公司介绍联系我们用户协议隐私条款
关注我们

Suppr 超能文献

核心技术专利:CN118964589B侵权必究
粤ICP备2023148730 号-1Suppr @ 2026

文献检索

告别复杂PubMed语法,用中文像聊天一样搜索,搜遍4000万医学文献。AI智能推荐,让科研检索更轻松。

立即免费搜索

文件翻译

保留排版,准确专业,支持PDF/Word/PPT等文件格式,支持 12+语言互译。

免费翻译文档

深度研究

AI帮你快速写综述,25分钟生成高质量综述,智能提取关键信息,辅助科研写作。

立即免费体验

在无溶剂条件下,铋介导的芳香羰基化合物的巴比耶型烯丙基化反应有明显的促进作用。

Noticeable facilitation of the bismuth-mediated Barbier-type allylation of aromatic carbonyl compounds under solvent-free conditions.

作者信息

Wada Shinobu, Hayashi Nobuyuki, Suzuki Hitomi

机构信息

Department of Chemistry, School of Science and Technology, Kwansei Gakuin University, Gakuen 2-1, Sanda 669-1337, Japan.

出版信息

Org Biomol Chem. 2003 Jun 21;1(12):2160-3. doi: 10.1039/b303783e.

DOI:10.1039/b303783e
PMID:12945908
Abstract

When milled together with bismuth shot in the presence of allyl halide, aromatic aldehydes readily underwent a Barbier-type allylation to afford the corresponding homoallyl alcohols in good yield. In contrast to the failure in solution reaction, aromatic ketones also underwent allylic carbonyl addition under solvent-free conditions to give the expected tertiary homoallyl alcohols in moderate to good yield.

摘要

在卤代烯丙基存在下与铋丸一起研磨时,芳香醛很容易发生巴比耶型烯丙基化反应,以良好的产率得到相应的高烯丙醇。与溶液反应失败不同,芳香酮在无溶剂条件下也能发生烯丙基羰基加成反应,以中等至良好的产率得到预期的叔高烯丙醇。

相似文献

1
Noticeable facilitation of the bismuth-mediated Barbier-type allylation of aromatic carbonyl compounds under solvent-free conditions.在无溶剂条件下,铋介导的芳香羰基化合物的巴比耶型烯丙基化反应有明显的促进作用。
Org Biomol Chem. 2003 Jun 21;1(12):2160-3. doi: 10.1039/b303783e.
2
Magnesium-Mediated Carbon-Carbon Bond Formation in Aqueous Media: Barbier-Grignard Allylation and Pinacol Coupling of Aldehydes.水相中镁介导的碳-碳键形成:醛的巴比耶-格氏烯丙基化反应和平纳醇偶联反应
J Org Chem. 1999 Apr 30;64(9):3230-3236. doi: 10.1021/jo982497p.
3
A convenient procedure for bismuth-mediated Barbier-type allylation of aldehydes in water containing fluoride ions.一种在含氟离子的水中铋介导的醛的巴比耶型烯丙基化的简便方法。
Org Biomol Chem. 2004 Mar 21;2(6):935-8. doi: 10.1039/b400179f. Epub 2004 Feb 25.
4
Pd(OAc)2/P(cC6H11)3-catalyzed allylation of aryl halides with homoallyl alcohols via retro-allylation.醋酸钯/三环己基膦催化芳基卤化物与高烯丙醇通过逆烯丙基化反应进行的烯丙基化反应。
J Am Chem Soc. 2007 Apr 11;129(14):4463-9. doi: 10.1021/ja067372d. Epub 2007 Mar 21.
5
Indium-mediated asymmetric barbier-type allylations: additions to aldehydes and ketones and mechanistic investigation of the organoindium reagents.铟介导的不对称巴尔比耶型烯丙基化反应:醛和酮的加成反应及有机铟试剂的反应机理研究。
J Org Chem. 2010 Feb 5;75(3):642-9. doi: 10.1021/jo902173j.
6
Metal-mediated allylation of enzymatically oxidized methyl α-D-galactopyranoside.金属介导的酶氧化甲基 α-D-吡喃半乳糖苷的烯丙基化反应。
Carbohydr Res. 2010 Dec 10;345(18):2610-5. doi: 10.1016/j.carres.2010.09.026. Epub 2010 Sep 27.
7
Photocatalytic Barbier reaction - visible-light induced allylation and benzylation of aldehydes and ketones.光催化巴比耶反应——可见光诱导的醛和酮的烯丙基化和苄基化反应
Chem Sci. 2018 Aug 2;9(36):7230-7235. doi: 10.1039/c8sc02038h. eCollection 2018 Sep 28.
8
Rhodium-catalyzed allyl transfer from homoallyl alcohols to aldehydes via retro-allylation followed by isomerization into ketones.铑催化下,通过逆烯丙基化反应,将高烯丙醇中的烯丙基转移至醛上,随后异构化为酮。
Org Lett. 2006 Jun 8;8(12):2515-7. doi: 10.1021/ol060710v.
9
Petasis Borono-Mannich reaction and allylation of carbonyl compounds via transient allyl boronates generated by palladium-catalyzed substitution of allyl alcohols. an efficient one-pot route to stereodefined alpha-amino acids and homoallyl alcohols.通过钯催化烯丙醇取代反应生成的瞬态烯丙基硼酸酯实现羰基化合物的Petasis硼-曼尼希反应和烯丙基化反应。一种立体定向合成α-氨基酸和高烯丙醇的高效一锅法路线。
J Am Chem Soc. 2007 Nov 7;129(44):13723-31. doi: 10.1021/ja074917a. Epub 2007 Oct 12.
10
The domino multicomponent allylation reaction for the stereoselective synthesis of homoallylic alcohols.用于立体选择性合成高烯丙醇的多米诺多组分烯丙基化反应。
Acc Chem Res. 2009 Feb 17;42(2):367-78. doi: 10.1021/ar800170y.

引用本文的文献

1
Mechanochemical Aerobic Activation of Metallic Copper for the Synthesis of 1,4-Allenynes.金属铜的机械化学需氧活化用于1,4-联烯炔的合成
ChemSusChem. 2025 Jul 1;18(13):e202500211. doi: 10.1002/cssc.202500211. Epub 2025 May 7.
2
Mechanical Activation of Zero-Valent Metal Reductants for Nickel-Catalyzed Cross-Electrophile Coupling.用于镍催化交叉亲电偶联的零价金属还原剂的机械活化
ACS Catal. 2022 Nov 4;12(21):13681-13689. doi: 10.1021/acscatal.2c03117. Epub 2022 Oct 25.
3
Bi-mediated allylation of aldehydes in [bmim][Br]: a mechanistic investigation.
在[bmim][Br]中铋介导的醛的烯丙基化反应:机理研究
Beilstein J Org Chem. 2018 Aug 22;14:2198-2203. doi: 10.3762/bjoc.14.193. eCollection 2018.
4
A Green Approach for Allylations of Aldehydes and Ketones: Combining Allylborate, Mechanochemistry and Lanthanide Catalyst.醛和酮烯丙基化的绿色方法:烯丙基硼酸酯、机械化学与镧系催化剂的结合
Molecules. 2016 Nov 16;21(11):1539. doi: 10.3390/molecules21111539.