Access the full text.
Sign up today, get DeepDyve free for 14 days.
K. Uneyama (2007)
Organofluorine Chemistry: Kenji/Organofluorine
C. Ni, Laijun Zhang, Jinbo Hu (2009)
Synthesis of fluorinated beta-ketosulfones and gem-disulfones by nucleophilic fluoroalkylation of esters and sulfinates with di- and monofluoromethyl sulfones.The Journal of organic chemistry, 74 10
P. Jeschke (2004)
The Unique Role of Fluorine in the Design of Active Ingredients for Modern Crop ProtectionChemBioChem, 5
Hou‐Jen Tsai (1996)
Synthesis of phenyl substituted fluoro-olefinsTetrahedron Letters, 37
G. Prakash, Sujith Chacko, Habiba Vaghoo, Nana Shao, Laxman Gurung, T. Mathew, G. Olah (2009)
Efficient nucleophilic fluoromethylation and subsequent transformation of alkyl and benzyl halides using fluorobis(phenylsulfonyl)methane.Organic letters, 11 5
K. Müller, Christoph Faeh, F. Diederich (2007)
Fluorine in Pharmaceuticals: Looking Beyond IntuitionScience, 317
Wei Zhang, Weizhou Huang, Jinbo Hu (2009)
Highly stereoselective synthesis of monofluoroalkenes from alpha-fluorosulfoximines and nitrones.Angewandte Chemie, 48 52
K. Uneyama (2006)
Organofluorine Chemistry
Z. Du, Melissa Haglund, L. Pratt, K. Erickson (1998)
Carbanionic Rearrangements of Halomethylenecyclobutanes. The Role of the HalogenJournal of Organic Chemistry, 63
(1991)
For selected reactions with FBSM as a reagent , see ( a )
S. Purrington, J. Pittman (1987)
The Preparation of α-Fluorosulfoxides and Vinyl FluoridesTetrahedron Letters, 28
Xiao Shen, Laijun Zhang, Yanchuan Zhao, Lingui Zhu, Guangyu Li, Jinbo Hu (2011)
Nucleophilic fluoromethylation of aldehydes with fluorobis(phenylsulfonyl)methane: the importance of strong Li-O coordination and fluorine substitution for C-C bond formation.Angewandte Chemie, 50 11
T. Furukawa, Y. Goto, Jumpei Kawazoe, Etsuko Tokunaga, Shuichi Nakamura, Yudong Yang, H. Du, A. Kakehi,, M. Shiro, N. Shibata (2010)
2-Fluoro-1,3-benzodithiole-1,1,3,3-tetraoxide: a reagent for nucleophilic monofluoromethylation of aldehydes.Angewandte Chemie, 49 9
Xiao Shen, C. Ni, Jinbo Hu (2012)
Nucleophilic Fluoroalkylation of α,β‐Unsaturated Carbonyl Compounds with α‐Fluorinated Sulfones: Investigation of the Reversibility of 1,2‐Additions and the Formation of 1,4‐AdductsHelvetica Chimica Acta, 95
I. Ojima (2009)
Fluorine in medicinal chemistry and chemical biology
Xiao Shen, Wei Zhang, C. Ni, Yucheng Gu, Jinbo Hu (2012)
Tuning the reactivity of difluoromethyl sulfoximines from electrophilic to nucleophilic: stereoselective nucleophilic difluoromethylation of aryl ketones.Journal of the American Chemical Society, 134 41
D. Michel, M. Schlosser (1996)
(ω-1)-Fluoroalk-(ω-1)-enoic Acids: Potential FungicidesSynthesis, 1996
P. Kirsch (2004)
Modern Fluoroorganic Chemistry
C. Ni, Laijun Zhang, Jinbo Hu (2008)
Nucleophilic fluoroalkylation of alpha,beta-enones, arynes, and activated alkynes with fluorinated sulfones: probing the hard/soft nature of fluorinated carbanions.The Journal of organic chemistry, 73 15
C. Ni, Ya Li, Jinbo Hu (2006)
Nucleophilic fluoroalkylation of epoxides with fluorinated sulfones.The Journal of organic chemistry, 71 18
Christophe Aïssa (2009)
Mechanistic Manifold and New Developments of the Julia–Kocienski ReactionEuropean Journal of Organic Chemistry, 2009
T. Taguchi, H. Yanai (2009)
Fluorinated Moieties for Replacement of Amide and Peptide BondsChemInform, 41
Shilei Zhang, Yinan Zhang, Yafei Ji, Hao Li, Wei Wang (2009)
Catalytic enantioselective conjugate addition of fluorobis(phenylsulfonyl)methane to enals: synthesis of chiral monofluoromethyl compounds.Chemical communications, 32
Xiao Shen, Wei Zhang, Lei Zhang, T. Luo, X. Wan, Yucheng Gu, Jinbo Hu (2012)
Enantioselective synthesis of cyclopropanes that contain fluorinated tertiary stereogenic carbon centers: a chiral α-fluoro carbanion strategy.Angewandte Chemie, 51 28
G. Prakash, F. Wang, Nana Shao, T. Mathew, G. Rasul, R. Haiges, Timothy Stewart, G. Olah (2009)
A persistent alpha-fluorocarbanion and its analogues: preparation, characterization, and computational study.Angewandte Chemie, 48 29
J. Baudin*, G. Hareau, S. Julia, O. Ruel (1991)
A direct synthesis of olefins by reaction of carbonyl compounds with lithio derivatives of 2-[alkyl- or (2'-alkenyl)- or benzyl-sulfonyl]-benzothiazolesTetrahedron Letters, 32
D. Burton, D. Cox (1983)
Wittig olefination via reaction of fluorine-containing phosphoranium salts and F-acyl fluorides. A new approach to fluoroolefin synthesisJournal of the American Chemical Society, 105
Wei Zhang, C. Ni, Jinbo Hu (2012)
Selective fluoroalkylation of organic compounds by tackling the "negative fluorine effect".Topics in current chemistry, 308
O. Wong, Yian Shi (2009)
Asymmetric epoxidation of fluoroolefins by chiral dioxirane. Fluorine effect on enantioselectivity.The Journal of organic chemistry, 74 21
M. Pagliaro, R. Ciriminna (2005)
New fluorinated functional materialsJournal of Materials Chemistry, 15
P. Blakemore, W. Cole, P. Kocieňski, A. Morley (1998)
A Stereoselective Synthesis of trans-1,2-Disubstituted Alkenes Based on the Condensation of Aldehydes with Metallated 1-Phenyl-1H-tetrazol-5-yl SulfonesSynlett, 1998
G. Landelle, Maxime Bergeron, Marc-Olivier Turcotte-Savard, J. Paquin (2011)
Synthetic approaches to monofluoroalkenes.Chemical Society reviews, 40 5
Lingui Zhu, C. Ni, Yanchuan Zhao, Jinbo Hu (2010)
1-tert-Butyl-1H-tetrazol-5-yl fluoromethyl sulfone (TBTSO2CH2F): a versatile fluoromethylidene synthon and its use in the synthesis of monofluorinated alkenes via Julia-Kocienski olefinationTetrahedron, 66
Shaoman Zhou, E. Kern, E. Gullen, Yung‐chi Cheng, J. Drach, S. Tamiya, H. Mitsuya, J. Žemlička (2006)
9-{[3-fluoro-2-(hydroxymethyl)cyclopropylidene]methyl}adenines and -guanines. Synthesis and antiviral activity of all stereoisomers1.Journal of medicinal chemistry, 49 20
Jian Lin, J. Welch (1998)
The stereoselective construction of fluoroalkenoates via the Peterson olefination reaction using tert-butyl α-fluoro-α-(trialkylsilyl)acetatesTetrahedron Letters, 39
Xian-hai Huang, Pi-yan He, Guo-qiang Shi (2000)
Highly stereoselective addition-elimination reaction of nucleophiles with ethyl 3,3-difluoro-2-The Journal of organic chemistry, 65 2
T. Fukuzumi, N. Shibata, M. Sugiura, H. Yasui, Shuichi Nakamura, T. Toru (2006)
Fluorobis(phenylsulfonyl)methane: a fluoromethide equivalent and palladium-catalyzed enantioselective allylic monofluoromethylation.Angewandte Chemie, 45 30
A highly stereoselective synthesis of tetrasubstituted monofluoroalkenes with aldehydes and fluorobis(phenylsulfonyl)methane (FBSM) in one pot has been developed. The reaction was amenable to para‐ and meta‐substituted aryl aldehydes, 2‐naphthaldehyde, and cinnamaldehyde, giving phenylsulfonyl‐substituted monofluoroalkenes in 40%–86% yields with 98/2–99/1 Z/E ratios. The presence of the sulfonyl group enables the further transformation of the products into more useful monofluoroalkenes.
Chinese Journal of Chemistry – Wiley
Published: Jul 1, 2013
Keywords: ; ; ; ;
Read and print from thousands of top scholarly journals.
Already have an account? Log in
Bookmark this article. You can see your Bookmarks on your DeepDyve Library.
To save an article, log in first, or sign up for a DeepDyve account if you don’t already have one.
Copy and paste the desired citation format or use the link below to download a file formatted for EndNote
Access the full text.
Sign up today, get DeepDyve free for 14 days.
All DeepDyve websites use cookies to improve your online experience. They were placed on your computer when you launched this website. You can change your cookie settings through your browser.