Iridium-Catalyzed X-H Insertions of Sulfoxonium Ylides

被引：151

作者：

Mangion, Ian K. ^{[1
]}

Nwamba, Ikenna K. ^{[1
]}

Shevlin, Michael ^{[1
]}

Huffman, Mark A. ^{[1
]}

机构：

[1] Merck & Co Inc, Dept Proc Res, Rahway, NJ 07065 USA

来源：

ORGANIC LETTERS | 2009年 / 11卷 / 16期

关键词：

METAL CARBENE TRANSFORMATIONS; ASYMMETRIC CYCLOPROPANATION; GENERAL-METHOD; N-H; COMPLEXES; DIAZOACETATES; DIAZOKETONES; ACTIVATION; OLEFINS;

D O I：

10.1021/ol901298p

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The unique reactivity of sulfoxonium ylides as a carbene source is described for a variety of X-H bond insertions, taking advantage of a simple, commercially available iridium catalyst. This method has applications in both intra- and intermolecular reactivity, including a practical ring-expansion strategy for lactams. The safety and stability of sulfoxonium ylides recommend them as preferable surrogates to traditional diazo ketones and esters.

引用

页码：3566 / 3569

页数：4

共 50 条

[31] Iridium-catalyzed direct borylation of phenacenes [J].

Hitosugi, Shunpei ;

Nakamura, Yuta ;

Matsuno, Taisuke ;

Nakanishi, Waka ;

Isobe, Hiroyuki .

TETRAHEDRON LETTERS, 2012, 53 (09) :1180-1182

[32] Iridium-Catalyzed Asymmetric Isomerization of Primary Allylic Alcohols [J].

Mantilli, Luca ;

Gerard, David ;

Torche, Sonya ;

Besnard, Celine ;

Mazet, Clement .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (28) :5143-5147

[33] Iridium-Catalyzed Undirected Homogeneous C-H Borylation Reaction [J].

Fernandez, Elena .

IRIDIUM CATALYSTS FOR ORGANIC REACTIONS, 2021, 69 :207-225

[34] Synthesis of Anthraquinones by Iridium-Catalyzed [2 [J].

Sawano, Takahiro ;

Toyoshima, Yuko ;

Takeuchi, Ryo .

INORGANICS, 2019, 7 (11)

[35] Iridium-Catalyzed Asymmetric Hydrogenation of Imines [J].

Baeza, Alejandro ;

Pfaltz, Andreas .

CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (13) :4003-4009

[36] Theoretical study on the mechanism of iridium-catalyzed γ-functionalization of primary alkyl C-H bonds [J].

Li, Zhe ;

Xia, Miaoren ;

Boyd, Russell J. .

CANADIAN JOURNAL OF CHEMISTRY, 2016, 94 (12) :1028-1037

[37] MOF-Supported Diphosphine Ligands for Iridium-Catalyzed C-H Borylation of Arenes [J].

Hilliard, Jordon S. ;

Murray, Daniel J. ;

Saha, Ankita ;

Goldberger, Joshua E. ;

Wade, Casey R. .

INORGANIC CHEMISTRY, 2025, 64 (14) :7127-7136

[38] Iridium-Catalyzed Site-Selective C-H Borylation of 2-Pyridones [J].

Miura, Wataru ;

Hirano, Koji ;

Miura, Masahiro .

SYNTHESIS-STUTTGART, 2017, 49 (21) :4745-4752

[39] Synthesis of Indoles and Pyrroles Utilizing Iridium Carbenes Generated from Sulfoxonium Ylides [J].

Vaitla, Janakiram ;

Bayer, Annette ;

Hopmann, Kathrin H. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (15) :4277-4281

[40] Ligand-Free Iridium-Catalyzed Borylation of Secondary Benzylic C-H Bonds [J].

Liu, Luhua ;

Du, Rongrong ;

Xu, Senmiao .

CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2021, 41 (04) :1572-1581

← 1 2 3 4 5 →