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Stereoselective synthesis of (E)- and (Z)-Fluoroalkenylboronates using 2-fluoroalkylideneiodonium ylides generated from (2-fluoro-1-alkenyl)iodonium salts.
J Org Chem. 2007 Dec 07; 72(25):9617-21.JO

Abstract

(E)- and (Z)-(fluoroalkenyl)boronates were prepared stereospecifically by the reaction of 2-fluoroalkylideneiodonium ylide generated from (E)- or (Z)-(2-fluoroalkenyl)iodonium salts with di(p-fluorophenoxy)alkylboranes, followed by transesterification to pinacol esters. The resulting pinacol esters of (fluoroalkenyl)boranes were used for the stereoselective synthesis of trisubstituted fluoroalkenes by cross-coupling reactions.

Authors+Show Affiliations

Guan T
Graduate School of Engineering, Hokkaido University, Sapporo 060-8628, Japan.
Yoshida M
No affiliation info available
Hara S
No affiliation info available

MeSH

AlkenesBoratesBoric AcidsBoronic AcidsIodineMolecular StructureOnium CompoundsSaltsStereoisomerism

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

17979292

Citation

Guan, Tong, et al. "Stereoselective Synthesis of (E)- and (Z)-Fluoroalkenylboronates Using 2-fluoroalkylideneiodonium Ylides Generated From (2-fluoro-1-alkenyl)iodonium Salts." The Journal of Organic Chemistry, vol. 72, no. 25, 2007, pp. 9617-21.
Guan T, Yoshida M, Hara S. Stereoselective synthesis of (E)- and (Z)-Fluoroalkenylboronates using 2-fluoroalkylideneiodonium ylides generated from (2-fluoro-1-alkenyl)iodonium salts. J Org Chem. 2007;72(25):9617-21.
Guan, T., Yoshida, M., & Hara, S. (2007). Stereoselective synthesis of (E)- and (Z)-Fluoroalkenylboronates using 2-fluoroalkylideneiodonium ylides generated from (2-fluoro-1-alkenyl)iodonium salts. The Journal of Organic Chemistry, 72(25), 9617-21.
Guan T, Yoshida M, Hara S. Stereoselective Synthesis of (E)- and (Z)-Fluoroalkenylboronates Using 2-fluoroalkylideneiodonium Ylides Generated From (2-fluoro-1-alkenyl)iodonium Salts. J Org Chem. 2007 Dec 7;72(25):9617-21. PubMed PMID: 17979292.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Stereoselective synthesis of (E)- and (Z)-Fluoroalkenylboronates using 2-fluoroalkylideneiodonium ylides generated from (2-fluoro-1-alkenyl)iodonium salts. AU - Guan,Tong, AU - Yoshida,Masanori, AU - Hara,Shoji, Y1 - 2007/11/03/ PY - 2007/11/6/pubmed PY - 2008/2/21/medline PY - 2007/11/6/entrez SP - 9617 EP - 21 JF - The Journal of organic chemistry JO - J Org Chem VL - 72 IS - 25 N2 - (E)- and (Z)-(fluoroalkenyl)boronates were prepared stereospecifically by the reaction of 2-fluoroalkylideneiodonium ylide generated from (E)- or (Z)-(2-fluoroalkenyl)iodonium salts with di(p-fluorophenoxy)alkylboranes, followed by transesterification to pinacol esters. The resulting pinacol esters of (fluoroalkenyl)boranes were used for the stereoselective synthesis of trisubstituted fluoroalkenes by cross-coupling reactions. SN - 0022-3263 UR - https://www.unboundmedicine.com/medline/citation/17979292/Stereoselective_synthesis_of__E___and__Z__Fluoroalkenylboronates_using_2_fluoroalkylideneiodonium_ylides_generated_from__2_fluoro_1_alkenyl_iodonium_salts_ DB - PRIME DP - Unbound Medicine ER -