Combining gold and palladium catalysis: One-pot access to pentasubstituted arenes from furan-yne and En-diyne substrates

Hashmi A.S.K.; Ghanbari M.; Rudolph M.; Rominger F.

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Combining gold and palladium catalysis: One-pot access to pentasubstituted arenes from furan-yne and En-diyne substrates

机译：结合金和钯催化作用：一锅接触呋喃-炔和恩-二炔底物的五取代芳烃

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A series of furan-yne systems was transformed into the corresponding tetrasubstituted annelated phenol derivatives that bear one bromo group. The two-step procedure consisted of a phenol synthesis and a subsequent electrophilic bromination with N-bromosuccinimide (NBS). The reactions can be performed in a one-pot procedure with the same precatalyst. The halogenation reaction is highly selective only in the presence of the gold catalyst. En-diyne substrates were also suitable starting materials; then the pentasubstituted aromatic core showed a completely different substitution pattern for the phenolic products. Furthermore, a one-pot protocol that consisted of a gold-catalyzed phenol synthesis, a gold-catalyzed halogenation reaction, and a palladium-catalyzed Suzuki coupling was established. The overall efficiency of this procedure was excellent and the substrate scope of the reaction was broad.

机译：将一系列呋喃-炔系统转化为带有一个溴代基团的相应四取代的退火苯酚衍生物。此两步程序包括苯酚合成和随后的N-溴琥珀酰亚胺（NBS）的亲电溴化。该反应可以用相同的预催化剂以一锅法进行。卤化反应仅在金催化剂存在下才具有高选择性。 En-二炔底物也是合适的起始原料。然后五取代的芳族核对酚类产品表现出完全不同的取代方式。此外，建立了由金催化的酚合成，金催化的卤化反应和钯催化的Suzuki偶联组成的一锅法。该方法的总效率极好，反应的底物范围广。

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《Chemistry: A European journal》 |2012年第26期|共7页
作者
Hashmi A.S.K.; Ghanbari M.; Rudolph M.; Rominger F.;
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正文语种 eng
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关键词
arenes; furans; gold; one-pot reaction; palladium;

机译：芳烃;呋喃;金;一锅法;钯;

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1. Combining gold and palladium catalysis: One-pot access to pentasubstituted arenes from furan-yne and En-diyne substrates [J] . Hashmi A.S.K., Ghanbari M., Rudolph M., Chemistry: A European journal . 2012,第26期

机译：结合金和钯催化作用：一锅接触呋喃-炔和恩-二炔底物的五取代芳烃
2. Gold catalysis: Domino reaction of En-diynes to highly substituted phenols [J] . Hashmi A.S.K., H?ffner T., Rudolph M., Chemistry: A European journal . 2011,第29期

机译：金催化：二炔与高取代酚的多米诺反应
3. One-Pot Asymmetric Nitro-Mannich/Hydroamination Cascades for the Synthesis of Pyrrolidine Derivatives: Combining Organocatalysis and Gold Catalysis [J] . David M. Barber, Andrej Duris, Amber L. Thompson ACS catalysis . 2014,第2期

机译：一锅不对称硝基曼尼希/加氢胺级联反应合成吡咯烷衍生物：结合有机催化和金催化。
4. One-pot Synthesis of Arylbutadienes from Arenes and Ethyl Propiolate Using a Palladium Catalyst with Bidentate Phosphine Ligands [C] . Juzo Oyamada, Tsugio Kitamura Symposium on Organometallic Chemistry . 2007

机译：使用钯催化剂与二齿膦配体的钯催化剂合成芳基和乙酸乙酯的芳基丁合成
5. I. Multicatalysis: Development of a Bismuth(III) triflate-catalyzed Nucleophilic addition/ Hydrofunctionalization Reaction in the Synthesis of Complex Heterocycles II. C--H Arylation of Arenes and Heteroarenes with Palladium-Carboxylate Catalysts: Identification of the Catalyst Resting State and the Crucial Role of Pivalate Ligand in Stabilization of the Catalyst III. C--H Arylation of Heteroarenes with Palladium-Carboxylate Catalysts: Importance of Phosphine Ligand for Basic Heteroarene Substrates IV. C--H Arylation of Heteroarenes with Palladium-Carboxylate Catalysts: Effect of the Properties of Basic Heteroarene Substrates on Direct Arylations. [D] . Tundel, Rachel E. 2011

机译：I.多催化作用：在复杂的杂环化合物的合成中三氟甲磺酸铋（III）催化的亲核加成/加氢官能化反应的发展。羰基钯催化剂对芳烃和杂芳烃的CH-H芳基化反应：催化剂静止状态的鉴定以及新戊酸酯配体在稳定催化剂中的关键作用III。羰基钯催化剂催化杂芳烃的CH芳基化：膦配体对基础杂芳烃基质的重要性IV。杂芳烃与钯-羧酸酯的CH芳基化：碱性杂芳烃底物性能对直接芳基化的影响。
6. One-Pot Asymmetric Nitro-Mannich/HydroaminationCascadesfor the Synthesis of Pyrrolidine Derivatives: Combining Organocatalysisand Gold Catalysis [O] . DavidM. Barber, §, Andrej Ďuriš, -1

机译：一锅不对称硝基曼尼希/氢化级联吡咯烷衍生物的合成：有机催化和金催化
7. One-Pot Asymmetric Nitro-Mannich/Hydroamination Cascades for the Synthesis of Pyrrolidine Derivatives: Combining Organocatalysis and Gold Catalysis. [O] . Barber, DM, Duriš, A, Thompson, AL, 2014

机译：用于合成吡咯烷衍生物的一锅不对称硝基曼尼希/加氨胺级联反应：有机催化和金催化的结合。

Combining gold and palladium catalysis: One-pot access to pentasubstituted arenes from furan-yne and En-diyne substrates

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