Coupling of Sulfoxonium Ylides with Arynes: A Direct Synthesis of Pro-Chiral Aryl Ketosulfoxonium Ylides and Its Application in the Preparation of α-Aryl Ketones

被引：76

作者：

Talero, Alexander Garay ^{[1
]}

Martins, Bruna Simoes ^{[1
]}

Burtoloso, Antonio C. B. ^{[1
]}

机构：

[1] Univ Sao Paulo, Inst Quim Sao Carlos, BR-13560970 Sao Carlos, SP, Brazil

来源：

ORGANIC LETTERS | 2018年 / 20卷 / 22期

基金：

巴西圣保罗研究基金会;

关键词：

DIAZO-CARBONYL-COMPOUNDS; H INSERTION REACTIONS; SULFUR YLIDES; FORMAL SYNTHESIS; SULFONIUM; ARYLATION; BONDS; FUNCTIONALIZATION; CYCLOPROPANATION; DECOMPOSITION;

D O I：

10.1021/acs.orglett.8b03126

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A general, mild, and versatile synthesis of the challenging alpha-aryl-beta-ketosulfoxonium ylides has been developed for the first time, substituting traditional methods starting from diazo compounds. The arylation of easily accessible beta-ketosulfoxonium ylides using aryne chemistry allowed the preparation of a large scope of the pro-chiral ylides in very good yields (40 examples; up to 85%). As applications, these ylides were smoothly converted into alpha-aryl ketones after desulfurization in good yields (up to 98%) as well as in other important derivatives.

引用

页码：7206 / 7211

页数：6

共 78 条

[1] Application of Sulfur Ylides in 1,2-Difunctionalization of Arynes via Insertion into a C-S σ-Bond [J].

Ahire, Milind M. ;

Thoke, Mahesh B. ;

Mhaske, Santosh B. .

ORGANIC LETTERS, 2018, 20 (03) :848-851

[2]

ANDO W, 1969, TETRAHEDRON LETT, P1979

[3] Anti-addition of Dimethylsulfoxonium Methylide to Acyclic α,β-Unsaturated Ketones and Its Application in Formal Synthesis of an Eicosanoid [J].

Angamuthu, Venkatachalam ;

Chang, Wen-Jung ;

Hou, Duen-Ren .

ACS OMEGA, 2017, 2 (08) :4088-4099

[4] A NOVEL ENTRY TO CARBENOID SPECIES VIA BETA-KETOSULFOXONIUM YLIDES [J].

BALDWIN, JE ;

ADLINGTON, RM ;

GODFREY, CRA ;

GOLLINS, DW ;

VAUGHAN, JG .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1993, (18) :1434-1435

[5] Cross-Coupling of α-Carbonyl Sulfoxonium Ylides with C-H Bonds [J].

Barday, Manuel ;

Janot, Christopher ;

Halcovitch, Nathan R. ;

Muir, James ;

Aissa, Christophe .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (42) :13117-13121

[6] Transition Metal-Catalyzed Direct Arylation of Substrates with Activated sp3-Hybridized C-H Bonds and Some of Their Synthetic Equivalents with Aryl Halides and Pseudohalides [J].

Bellina, Fabio ;

Rossi, Renzo .

CHEMICAL REVIEWS, 2010, 110 (02) :1082-1146

[7] Advances in the Enantioselective Metal-catalyzed N-H and O-H Insertion Reactions with Diazocarbonyl Compounds [J].

Burtoloso, Antonio C. B. ;

Santiago, Joao V. ;

Bernardim, Barbara ;

Talero, Alexander G. .

CURRENT ORGANIC SYNTHESIS, 2015, 12 (05) :650-659

[8] Sulfoxonium and Sulfonium Ylides as Diazocarbonyl Equivalents in Metal-Catalyzed Insertion Reactions [J].

Burtoloso, Antonio C. B. ;

Dias, Rafael M. P. ;

Leonarczyk, Ives A. .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2013, 2013 (23) :5005-5016

[9] Catalytic Enantioselective α-Arylation of Carbonyl Compounds [J].

Burtoloso, Antonio C. B. .

SYNLETT, 2009, (02) :320-327

[10] Living polymerization of sulfur ylides. Synthesis of terminally functionalized and telechelic polymethylene [J].

Busch, BB ;

Staiger, CL ;

Stoddard, JM ;

Shea, KJ .

MACROMOLECULES, 2002, 35 (22) :8330-8337

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