Dual Gold Catalysis: Synthesis of Polycyclic Compounds via C-H Insertion of Gold Vinylidenes

被引：61

作者：

Wieteck, Marcel ^{[1
]}

Tokimizu, Yusuke ^{[2
]}

Rudolph, Matthias ^{[1
]}

Rominger, Frank ^{[1
]}

Ohno, Hiroaki ^{[2
]}

Fujii, Nobutaka ^{[2
]}

Hashmi, A. Stephen K. ^{[1
,3
]}

机构：

[1] Heidelberg Univ, Organ Chem Inst, D-69120 Heidelberg, Germany

[2] Kyoto Univ, Grad Sch Pharmaceut Sci, Sakyo Ku, Kyoto 6068501, Japan

[3] King Abdulaziz Univ, Dept Chem, Fac Sci, Jeddah 21589, Saudi Arabia

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2014年 / 20卷 / 49期

基金：

日本学术振兴会;

关键词：

alkynes; CH insertion; gold; vinylidene ligands; polycycles; HOMOGENEOUS CATALYSIS; ALKYNES; CYCLIZATIONS; ACTIVATION; 3-SILYLOXY-1,5-ENYNES; HYDROARYLATION; PRECATALYSTS; HETEROCYCLES; CARBOCYCLES; DERIVATIVES;

D O I：

10.1002/chem.201404987

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

New and interesting polycyclic compounds have been synthesized from non-conjugated diyne systems by dual gold catalysis. A quaternary carbon center in the backbone and the accompanying Thorpe-Ingold effect enabled the unprecedented insertion of sp(3) and sp(2) CH bonds that for the first time were incorporated within the backbone of the diyne system and allowed the construction of complex polycyclic carbon scaffolds inaccessible by previous approaches in which the CH bonds for the insertion were situated at the other end of the alkyne.

引用

页码：16331 / 16336

页数：6

共 50 条

[41] Dual Gold Catalysis: Synthesis of Fluorene Derivatives from Diynes
Bucher, Janina
Wurm, Thomas
Taschinski, Svenja
Sachs, Eleni
Ascough, David
Rudolph, Matthias
Rominger, Frank
Hashmi, A. Stephen K.
ADVANCED SYNTHESIS & CATALYSIS, 2017, 359 (02) : 225 - 233
[42] Gold-mediated C-H bond functionalisation
Boorman, Tanya C.
Larrosa, Igor
CHEMICAL SOCIETY REVIEWS, 2011, 40 (04) : 1910 - 1925
[43] Gold-catalyzed reactions of C-H bonds
Skouta, Rachid
Li, Chao-Jun
TETRAHEDRON, 2008, 64 (22) : 4917 - 4938
[44] ORGANOMETALLIC CHEMISTRY C-H carboxylation takes gold
Dalton, Derek M.
Rovis, Tomislav
NATURE CHEMISTRY, 2010, 2 (09) : 710 - 711
[45] Gold(I)-Mediated C-H Activation of Arenes
Lu, Pengfei
Boorman, Tanya C.
Slawin, Alexandra M. Z.
Larrosa, Igor
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (16) : 5580 - +
[46] On Gold-Mediated C-H Activation Processes
de Haro, Teresa
Nevado, Cristina
SYNTHESIS-STUTTGART, 2011, (16): : 2530 - 2539
[47] Direct Observation of Aryl Gold(I) Carbenes that Undergo Cyclopropanation, C-H Insertion, and Dimerization Reactions
Garcia-Morales, Cristina
Pei, Xiao-Li
Toro, Juan M. Sarria
Echavarren, Antonio M.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (12) : 3957 - 3961
[48] Gold vs Rhodium Catalysis: Tuning Reactivity through Catalyst Control in the C-H Alkynylation of Isoquinolones
Shaikh, Aslam C.
Shinde, Dinesh R.
Patil, Nitin T.
ORGANIC LETTERS, 2016, 18 (05) : 1056 - 1059
[49] Highly Site-Selective Direct C-H Bond Functionalization of Phenols with α-Aryl-α-diazoacetates and Diazooxindoles via Gold Catalysis
Yu, Zhunzhun
Ma, Ben
Chen, Mingjin
Wu, Hai-Hong
Liu, Lu
Zhang, Junliang
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (19) : 6904 - 6907
[50] Aliphatic C-H alkylation via photoredox catalysis
Morton, Carla
Choi, Gilbert
Zhu, Qilei
Knowles, Robert
Alexanian, Erik
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2018, 256

← 1 2 3 4 5 →