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本文引用的文献

1
Nickel-Catalyzed Addition of Aryl Bromides to Aldehydes To Form Hindered Secondary Alcohols.镍催化芳基溴与醛加成反应合成位阻仲醇。
J Am Chem Soc. 2019 Feb 6;141(5):1823-1827. doi: 10.1021/jacs.8b13709. Epub 2019 Jan 29.
2
Intermolecular Metal-Catalyzed Reductive Coupling of Dienes, Allenes, and Enynes with Carbonyl Compounds and Imines.分子间金属催化的二烯、丙二烯和炔与羰基化合物和亚胺的还原偶联。
Chem Rev. 2018 Jun 27;118(12):6026-6052. doi: 10.1021/acs.chemrev.8b00213. Epub 2018 Jun 13.
3
Catalytic Enantioselective Carbonyl Allylation and Propargylation via Alcohol-Mediated Hydrogen Transfer: Merging the Chemistry of Grignard and Sabatier.通过醇介导的氢转移实现的手性催化羰基烯丙基化和炔丙基化:格氏试剂和萨巴蒂埃反应的化学融合。
Acc Chem Res. 2017 Sep 19;50(9):2371-2380. doi: 10.1021/acs.accounts.7b00308. Epub 2017 Aug 9.
4
Direct Aldehyde C-H Arylation and Alkylation via the Combination of Nickel, Hydrogen Atom Transfer, and Photoredox Catalysis.通过镍、氢原子转移和光氧化还原催化的组合实现直接醛 C-H 芳基化和烷基化。
J Am Chem Soc. 2017 Aug 23;139(33):11353-11356. doi: 10.1021/jacs.7b07078. Epub 2017 Aug 14.
5
Metal-catalyzed reductive coupling of olefin-derived nucleophiles: Reinventing carbonyl addition.金属催化的烯烃衍生亲核试剂的还原偶联:羰基加成反应的革新
Science. 2016 Oct 21;354(6310). doi: 10.1126/science.aah5133.
6
Nickel-Catalyzed Reductive Couplings.镍催化的还原偶联反应。
Top Curr Chem (Cham). 2016 Aug;374(4):43. doi: 10.1007/s41061-016-0042-2. Epub 2016 Jun 23.
7
Palladium-Catalyzed Environmentally Benign Acylation.钯催化的环境友好型酰化反应。
J Org Chem. 2016 Aug 5;81(15):6409-23. doi: 10.1021/acs.joc.6b01064. Epub 2016 Jul 19.
8
Reductive Cyclization of Halo-Ketones to Form 3-Hydroxy-2-Oxindoles Palladium Catalyzed Hydrogenation: A Hydrogen-Mediated Grignard Addition.卤代酮还原环化形成3-羟基-2-氧化吲哚 钯催化氢化:氢介导的格氏加成反应
Tetrahedron. 2015 Sep 2;71(35):5776-5780. doi: 10.1016/j.tet.2015.05.085.
9
Dialkyl Ether Formation by Nickel-Catalyzed Cross-Coupling of Acetals and Aryl Iodides.镍催化乙缩醛与芳基碘的交叉偶联反应生成二烷基醚
Angew Chem Int Ed Engl. 2015 Aug 17;54(34):9876-80. doi: 10.1002/anie.201503936. Epub 2015 Jul 15.
10
Vinylation of aldehydes using Mn/Cr alloy and a N4 -ligand/Ni(II) -catalyst.使用锰/铬合金和N4配体/镍(II)催化剂对醛进行乙烯基化反应。
Chemistry. 2015 Apr 13;21(16):6057-61. doi: 10.1002/chem.201500024. Epub 2015 Mar 11.

铑催化的通过甲酸盐介导的转移氢化的醛芳基化反应:超越格氏试剂/野崎-桥本-岸反应加成中的金属还原剂。

Rhodium-Catalyzed Aldehyde Arylation via Formate-Mediated Transfer Hydrogenation: Beyond Metallic Reductants in Grignard/Nozaki-Hiyami-Kishi-Type Addition.

机构信息

Department of Chemistry , University of Texas at Austin , Austin , Texas 78712 , United States.

Discovery Chemistry Research and Technologies , Eli Lilly and Company Limited , Erl Wood Manor , Windlesham , Surrey GU20 6PH , United Kingdom.

出版信息

J Am Chem Soc. 2019 Feb 6;141(5):1828-1832. doi: 10.1021/jacs.8b13652. Epub 2019 Jan 29.

DOI:10.1021/jacs.8b13652
PMID:30693768
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC6376962/
Abstract

The first intermolecular carbonyl arylations via transfer hydrogenative reductive coupling are described. Using rhodium catalysts modified by BuPMe, sodium formate-mediated reductive coupling of aryl iodides with aldehydes occurs in a chemoselective fashion in the presence of protic functional groups and lower halides. This work expands the emerging paradigm of transfer hydrogenative coupling as an alternative to pre-formed carbanions or metallic reductants in C═X addition.

摘要

本文首次描述了通过转移氢还原偶联实现的第一个分子间羰基芳基化反应。在质子官能团和低级卤化物存在的情况下,使用 BuPMe 修饰的铑催化剂,芳基碘化物与醛在甲酸钠介导下发生化学选择性还原偶联。这项工作扩展了转移氢还原偶联作为 C=X 加成中预形成的碳负离子或金属还原剂替代物的新兴范例。