Titanium reagents for the synthesis of 2-substituted benzo[b]thiophenes on the solid phase

The Journal of Organic Chemistry
Christine F Roberts, Richard C Hartley

Abstract

Titanium(IV) benzylidenes (Schrock carbenes) bearing a masked sulfur nucleophile in the ortho position were generated from thioacetals with use of low-valent titanocene complex Cp(2)Ti[P(OEt)(3)](2) and alkylidenated Merrifield resin-bound esters to give enol ethers. Treatment of the resin-bound enol ethers with a 5:5:90 mixture of TFA, TFAA, and dichloromethane led to cleavage from resin, removal of the tert-butyldimethylsilyl (TBDMS) protecting group, and concomitant cyclization to complete the traceless solid-phase synthesis (SPS) of benzothiophenes. Switching the nature of the linker from acid-stable to acid-sensitive ensured good purity.

References

Apr 1, 1996·Bioorganic & Medicinal Chemistry·D H BoschelliD J Schrier
May 18, 1999·Bioorganic & Medicinal Chemistry Letters·K G PinneyE Hamel
Dec 28, 1999·Bioorganic & Medicinal Chemistry Letters·B H NormanJ J Starling
Mar 27, 2001·Angewandte Chemie·Alex C. Comely, Susan E. Gibson
Jul 19, 2001·Bioorganic & Medicinal Chemistry Letters·W D ShraderG Carr
Aug 31, 2001·Bioorganic & Medicinal Chemistry Letters·B L FlynnM K Jung
Jan 10, 2002·Chemical Reviews·Viktor Krchnák, Mark W Holladay
Jul 11, 2002·Chemical Reviews·Paul BlaneyVisuvanathar Sridharan
Jan 18, 2003·The Journal of Organic Chemistry·Calum MacleodRichard C Hartley
Nov 7, 2003·Organic Letters·Gordon J McKiernan, Richard C Hartley
Nov 11, 2003·Journal of Combinatorial Chemistry·Roland E Dolle

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Citations

Nov 11, 2008·Chemical Communications : Chem Comm·Kiyofumi InamotoTakayuki Doi
Jul 11, 2019·Chemical Communications : Chem Comm·Xuekun WangXinghai Ning
Jun 20, 2015·Acta Crystallographica. Section E, Crystallographic Communications·N C SandhyaS Ananda
Jan 25, 2020·Current Organic Synthesis·Navjeet Kaur
Jul 4, 2009·The Journal of Organic Chemistry·Prabal P SinghH Junjappa
Feb 5, 2011·The Journal of Organic Chemistry·Daniel J SmithJoel P Schneider

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