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金催化 C-C 多重键加成反应的最新进展。

Recent advances in the gold-catalyzed additions to C-C multiple bonds.

机构信息

State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai 201203, China.

出版信息

Beilstein J Org Chem. 2011;7:897-936. doi: 10.3762/bjoc.7.103. Epub 2011 Jul 4.

DOI:10.3762/bjoc.7.103
PMID:21804887
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC3135236/
Abstract

C-O, C-N and C-C bonds are the most widespread types of bonds in nature, and are the cornerstone of most organic compounds, ranging from pharmaceuticals and agrochemicals to advanced materials and polymers. Cationic gold acts as a soft and carbophilic Lewis acid and is considered one of the most powerful activators of C-C multiple bonds. Consequently, gold-catalysis plays an important role in the development of new strategies to form these bonds in more convenient ways. In this review, we highlight recent advances in the gold-catalyzed chemistry of addition of X-H (X = O, N, C) bonds to C-C multiple bonds, tandem reactions, and asymmetric additions. This review covers gold-catalyzed organic reactions published from 2008 to the present.

摘要

C-O、C-N 和 C-C 键是自然界中最广泛存在的键类型，也是大多数有机化合物的基石，这些有机化合物的范围涵盖从药物和农用化学品到先进材料和聚合物。阳离子金作为一种柔软的亲电路易斯酸，被认为是最强的 C-C 多重键活化剂之一。因此，金催化在开发以更方便的方式形成这些键的新策略方面发挥着重要作用。在这篇综述中，我们重点介绍了近年来在 C-C 多重键加成 X-H（X=O、N、C）键的金催化化学、串联反应和不对称加成方面的最新进展。本综述涵盖了自 2008 年以来发表的金催化有机反应。

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5
Gold-catalyzed rearrangements: reaction pathways using 1-alkenyl-2-alkynylcyclopropane substrates.金催化重排反应：使用1-烯基-2-炔基环丙烷底物的反应途径
Angew Chem Int Ed Engl. 2011 Feb 25;50(9):2107-10. doi: 10.1002/anie.201007795. Epub 2011 Jan 24.
6
Enantioselective gold-catalyzed functionalization of unreactive sp3 C-H bonds through a redox-neutral domino reaction.手性金催化的通过氧化还原中性级联反应对非活性 sp3 C-H 键的功能化。
Chemistry. 2011 Mar 7;17(11):3101-4. doi: 10.1002/chem.201100019. Epub 2011 Feb 15.
7
Gold(I)-catalyzed intramolecular amination of allylic alcohols with alkylamines.金（I）催化的烯丙醇与烷基胺的分子内胺化反应。
Org Lett. 2011 Mar 18;13(6):1334-7. doi: 10.1021/ol103175w. Epub 2011 Feb 11.
8
Silver- and gold-mediated domino transformation: a strategy for synthesizing benzo[e]indolo[1,2-a]pyrrolo/pyrido[2,1-c][1,4]diazepine-3,9-diones.银和金介导的多米诺转化：一种合成苯并[e]吲哚[1,2-a]吡咯并/吡啶[2,1-c][1,4]二氮杂环庚三酮-3,9-二酮的策略。
J Org Chem. 2011 Mar 4;76(5):1239-49. doi: 10.1021/jo101727r. Epub 2011 Feb 3.
9
A general procedure for the synthesis of enones via gold-catalyzed Meyer-Schuster rearrangement of propargylic alcohols at room temperature.一种在室温下通过金催化炔丙醇的 Meyer-Schuster 重排反应合成烯酮的通用方法。
J Org Chem. 2011 Mar 4;76(5):1479-82. doi: 10.1021/jo102263t. Epub 2011 Jan 25.
10
Direct synthesis of fused indoles by gold-catalyzed cascade cyclization of diynes.金催化二炔的级联环化直接合成稠合吲哚。
J Org Chem. 2011 Mar 4;76(5):1212-27. doi: 10.1021/jo102507c. Epub 2011 Jan 21.