Difluoromethyl 2-Pyridyl Sulfone: A New gem-Difluoroolefination Reagent for Aldehydes and Ketones

被引：201

作者：

Zhao, Yanchuan ^{[1
]}

Huang, Weizhou ^{[1
]}

Zhu, Lingui ^{[1
]}

Hu, Jinbo ^{[1
]}

机构：

[1] Chinese Acad Sci, Shanghai Inst Organ Chem, Key Lab Organofluorine Chem, Shanghai 200032, Peoples R China

来源：

ORGANIC LETTERS | 2010年 / 12卷 / 07期

基金：

中国国家自然科学基金;

关键词：

CRAFTS-TYPE CYCLIZATION; CARBONYL-COMPOUNDS; NUCLEOPHILIC FLUOROALKYLATION; FLUORINATED SULFONES; INHIBITORS; CONVERSION; EFFICIENT; OLEFINS;

D O I：

10.1021/ol100090r

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Difluoromethyl 2-pyridyl sulfone, a previously unknown compound, was found to act as a novel and efficient gem-difluoroolefination reagent for both aldehydes and ketones. It was found that the fluorinated sulfinate intermediate in the reaction is relatively stable, which can be observed by F-19 NMR and trapped with CH3I.

引用

页码：1444 / 1447

页数：4

共 43 条

[1] Mechanistic Manifold and New Developments of the Julia-Kocienski Reaction
Aissa, Christophe
[J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2009, 2009 (12) : 1831 - 1844
[2] Highly efficient and stereoselective Julia-Kocienski protocol for the synthesis of α-fluoro-α,β-unsaturated esters and Weinreb amides employing 3,5-bis(trifluoromethyl)phenyl (BTFP) sulfones
Alonso, Diego A.
Fuensanta, Monica
Gomez-Bengoa, Enrique
Najera, Carmen
[J]. ADVANCED SYNTHESIS & CATALYSIS, 2008, 350 (11-12) : 1823 - 1829
[3] SSR182289A, a selective and potent orally active thrombin inhibitor
Altenburger, JM
Lassalle, GY
Matrougui, M
Galtier, D
Jetha, JC
Bocskei, Z
Berry, CN
Lunven, C
Lorrain, J
Herault, JP
Schaeffer, P
O'Connor, SE
Herbert, JM
[J]. BIOORGANIC & MEDICINAL CHEMISTRY, 2004, 12 (07) : 1713 - 1730
[4] Bgu J.-P., 2008, Bioorganic and Medicinal Chemistry of Fluorine
[5] The modified Julia olefination:: alkene synthesis via the condensation of metallated heteroarylalkylsulfones with carbonyl compounds
Blakemore, PR
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2002, (23): : 2563 - 2585
[6] Chambers R.D., 1997, ORGANOFLUORINE CHEM
[7] DIFLUOROMETHYLDIPHENYLPHOSPHINE OXIDE - A NEW REAGENT FOR CONVERSION OF CARBONYL-COMPOUNDS TO 1,1-DIFLUOROOLEFINS
EDWARDS, ML
STEMERICK, DM
JARVI, ET
MATTHEWS, DP
MCCARTHY, JR
[J]. TETRAHEDRON LETTERS, 1990, 31 (39) : 5571 - 5574
[8] FUQUA SA, 1964, TETRAHEDRON LETT, P1461
[9] High-yield synthesis of fluorinated benzothiazolyl sulfones: General synthons for fluoro-julia olefinations
Ghosh, AK
Zajc, B
[J]. ORGANIC LETTERS, 2006, 8 (08) : 1553 - 1556
[10] Fluorinated 1-Phenyl-1H-tetrazol-5-yl Sulfone Derivatives as General Reagents for Fluoroalkylidene Synthesis
Ghosh, Arun K.
Zajc, Barbara
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (22) : 8531 - 8540

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