Chemoselective α-Methylenation of Aromatic Ketones Using the NaAuCl4/Selectfluor/DMSO System

被引：21

作者：

Zhu, Hongbo ^{[1
]}

Meng, Xin ^{[1
]}

Zhang, Yanhui ^{[1
]}

Chen, Guang ^{[1
,2
]}

Cao, Ziping ^{[1
,2
]}

Sun, Xuejun ^{[1
,2
]}

You, Jinmao ^{[1
,2
]}

机构：

[1] Qufu Normal Univ, Sch Chem & Chem Engn, Qufu 273165, Shandong, Peoples R China

[2] Key Lab Pharmaceut Intermediates & Anal Nat Med, Shandong Key Lab Life Organ Anal, Qufu 273165, Shandong, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2017年 / 82卷 / 23期

关键词：

ALPHA; BETA-UNSATURATED CARBONYL-COMPOUNDS; ALKYNYL-SUBSTITUTED ARYLALDEHYDES; MEYER-SCHUSTER REARRANGEMENT; MEDIATED DOMINO REACTION; METAL-FREE; REGIOSELECTIVE SYNTHESIS; PROPARGYL ALCOHOLS; CONJUGATED DIENES; MICHAEL-ADDITION; ALLYLIC ALCOHOLS;

D O I：

10.1021/acs.joc.7b01790

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Gold-catalyzed chemoselective alpha-methylenation of aromatic ketones was developed through the use of Selectfluor as a methylenating agent. A variety of useful 1,2-disubstituted propenone derivatives can be prepared in good yields via the present protocol. This reaction features a simple operation, good functional group tolerance, and broad scope of substrates.

引用

页码：12059 / 12065

页数：7

共 77 条

[1] Metal-Free Michael-Addition-Initiated Three-Component Reaction for the Regioselective Synthesis of Highly Functionalized Pyridines: Scope, Mechanistic Investigations and Applications [J].

Allais, Christophe ;

Lieby-Muller, Frederic ;

Rodriguez, Jean ;

Constantieux, Thierry .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2013, 2013 (19) :4131-4145

[2] Enantioselective NHC-Catalyzed Redox [4+2]-Hetero-Diels-Alder Reactions Using α,β-Unsaturated Trichloromethyl Ketones as Amide Equivalents [J].

Attaba, Nassilia ;

Taylor, James E. ;

Slawin, Alexandra M. Z. ;

Smith, Andrew D. .

JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (19) :9728-9739

[3] Harnessing the Versatile Reactivity of Propargyl Alcohols and their Derivatives for Sustainable Complex Molecule Synthesis [J].

Ayers, Benjamin James ;

Chan, Philip Wai Hong .

SYNLETT, 2015, 26 (10) :1305-1339

[4] The Heck coupling reaction using aryl vinyl ketones: Synthesis of flavonoids [J].

Bianco, A ;

Cavarischia, C ;

Guiso, M .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2004, 2004 (13) :2894-2898

[5] Efficient, direct α-methylenation of carbonyls mediated by diisopropylammonium trifluoroacetate [J].

Bugarin, Alejandro ;

Jones, Kyle D. ;

Connell, Brian T. .

CHEMICAL COMMUNICATIONS, 2010, 46 (10) :1715-1717

[6] Metal-catalyzed transformations of propargylic alcohols into α,β-unsaturated carbonyl compounds: from the Meyer-Schuster and Rupe rearrangements to redox isomerizations [J].

Cadierno, Victorio ;

Crochet, Pascale ;

Garcia-Garrido, Sergio E. ;

Gimeno, Jose .

DALTON TRANSACTIONS, 2010, 39 (17) :4015-4031

[7]

Cao D., 2016, ORG CHEM, V81, P9973

[8]

Cao Z., 2016, J CHEM EUR J, V22, P16979

[9] Silver-Catalyzed Domino Reaction of ortho-Carbonylated Alkynyl-Substituted Arylaldehydes with Conjugated Dienes: Stereoselective Access to Indanone-Fused Cyclohexenes [J].

Cao, Ziping ;

Zhu, Hongbo ;

Meng, Xin ;

Tian, Laijin ;

Chen, Guang ;

Sun, Xuejun ;

You, Jinmao .

JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (24) :12401-12407

[10] Gold-catalyzed π-directed regioselective cyclization of bis(o-alkynyl benzyl alcohols): rapid access to dihydroisobenzofuran derivatives [J].

Cao, Ziping ;

Li, Shan ;

Li, Jie ;

Meng, Xin ;

Zhang, Huaqing ;

Sun, Xuejun ;

You, Jinmao .

NEW JOURNAL OF CHEMISTRY, 2016, 40 (10) :8211-8215

← 1 2 3 4 5 6 7 8 →