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以芳香醛为α-烷氧基烷基阴离子的烯丙基交叉偶联反应。

Allylic cross-coupling using aromatic aldehydes as α-alkoxyalkyl anions.

作者信息

Yuasa Akihiro, Nagao Kazunori, Ohmiya Hirohisa

机构信息

Division of Pharmaceutical Sciences, Graduate School of Medical Sciences, Kanazawa University, Kakuma-machi, Kanazawa 920-1192, Japan.

出版信息

Beilstein J Org Chem. 2020 Feb 7;16:185-189. doi: 10.3762/bjoc.16.21. eCollection 2020.

DOI:10.3762/bjoc.16.21
PMID:32117475
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC7034225/
Abstract

The allylic cross-coupling using aromatic aldehydes as α-alkoxyalkyl anions is described. The synergistic palladium/copper-catalyzed reaction of aromatic aldehydes, allylic carbonates, and a silylboronate produces the corresponding homoallylic alcohol derivatives. This process involves the catalytic formation of a nucleophilic α-silyloxybenzylcopper(I) species and the subsequent palladium-catalyzed allylic substitution.

摘要

描述了以芳香醛作为α-烷氧基烷基阴离子的烯丙基交叉偶联反应。芳香醛、烯丙基碳酸酯和甲硅烷基硼酸酯在钯/铜协同催化下反应生成相应的高烯丙醇衍生物。该过程涉及亲核性α-甲硅烷氧基苄基铜（I）物种的催化形成以及随后的钯催化烯丙基取代反应。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b8d2/7034225/7d144628432c/Beilstein_J_Org_Chem-16-185-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b8d2/7034225/fb8f18143b41/Beilstein_J_Org_Chem-16-185-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b8d2/7034225/cf5c1dd87a8a/Beilstein_J_Org_Chem-16-185-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b8d2/7034225/c9d58d5c6b4d/Beilstein_J_Org_Chem-16-185-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b8d2/7034225/99644110883b/Beilstein_J_Org_Chem-16-185-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b8d2/7034225/7d144628432c/Beilstein_J_Org_Chem-16-185-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b8d2/7034225/fb8f18143b41/Beilstein_J_Org_Chem-16-185-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b8d2/7034225/cf5c1dd87a8a/Beilstein_J_Org_Chem-16-185-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b8d2/7034225/c9d58d5c6b4d/Beilstein_J_Org_Chem-16-185-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b8d2/7034225/99644110883b/Beilstein_J_Org_Chem-16-185-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b8d2/7034225/7d144628432c/Beilstein_J_Org_Chem-16-185-g006.jpg

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本文引用的文献

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J Am Chem Soc. 2019 Feb 27;141(8):3664-3669. doi: 10.1021/jacs.8b13309. Epub 2019 Jan 31.
2
Asymmetric Catalysis Using Aromatic Aldehydes as Chiral α-Alkoxyalkyl Anions.使用芳香醛作为手性 α-烷氧基烷基阴离子的不对称催化。
J Am Chem Soc. 2019 Jan 9;141(1):113-117. doi: 10.1021/jacs.8b11495. Epub 2018 Dec 20.
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Bimetallic catalysis for C-C and C-X coupling reactions.用于碳-碳和碳-卤键偶联反应的双金属催化
Chem Sci. 2017 Mar 1;8(3):1705-1718. doi: 10.1039/c6sc05556g. Epub 2017 Jan 16.
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Synergistic palladium/copper-catalyzed Csp-Csp cross-couplings using aldehydes as latent α-alkoxyalkyl anion equivalents.协同钯/铜催化的 Csp-Csp 交叉偶联反应，使用醛作为潜在的 α-烷氧基烷基阴离子等价物。
Chem Commun (Camb). 2018 Jun 19;54(50):6776-6779. doi: 10.1039/c8cc01055b.
5
Asymmetric Hydroarylation of Vinylarenes Using a Synergistic Combination of CuH and Pd Catalysis.使用 CuH 和 Pd 催化的协同组合对乙烯基芳烃进行不对称氢芳基化反应。
J Am Chem Soc. 2016 Jul 13;138(27):8372-5. doi: 10.1021/jacs.6b04566. Epub 2016 Jul 1.
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A Cu/Pd Cooperative Catalysis for Enantioselective Allylboration of Alkenes.铜/钯协同催化对映选择性烯丙基硼化反应。
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