Multigram-Scale Synthesis of a gem-Difluoro-Substituted 4,5,6,7-Tetrahydrobenzo[c]thiophen-4-one Heterocycle via Oxidative Chlorination and Radical Smiles Rearrangement DOI
Craig Jamieson, Martyn C. Henry,

Jack Q. Anderson

et al.

Synlett, Journal Year: 2023, Volume and Issue: unknown

Published: Aug. 14, 2023

Abstract We report an optimized synthetic route towards a functionalized 4,5,6,7-tetrahydrobenzo[c]thiophene heterocycle bearing gem-difluoromethylene moiety in 4 steps with overall yield of 43%. The CF2 fragment was incorporated using building block approach, by coupling appropriate fluorinated alcohol C-3 sulfonyl chloride, synthesized via oxidative chlorination exocyclic benzyl thioether. Visible-light-mediated Smiles rearrangement the resulting fluorosulfonate ester then furnishes desired thiophene scaffold.

Language: Английский

Synthesis of β-tosyloxylated gem-difluoroalkanes via sulfonyloxy migration DOI Creative Commons

Fang‐Hai Tu,

Yi Wang, Zhan Li

et al.

Cell Reports Physical Science, Journal Year: 2022, Volume and Issue: 3(12), P. 101194 - 101194

Published: Dec. 1, 2022

Language: Английский

Citations

2
Catalytic, Regioselective 1,4‐Fluorodifunctionalization of Dienes DOI Creative Commons

You‐Jie Yu,

Michael Schäfer,

Constantin G. Daniliuc

et al.

Angewandte Chemie, Journal Year: 2022, Volume and Issue: 135(1)

Published: Nov. 8, 2022

Abstract A catalysis‐based regioselective 1,4‐fluorofunctionalization of trifluoromethyl substituted 1,3‐dienes has been developed to access compact, highly functionalized products. The process allows E , Z ‐mixed dienes be processed a single ‐alkene isomer, and leverages an inexpensive operationally convenient I(I)/I(III) catalysis platform. first example catalytic 1,4‐difluorination is disclosed subsequently evolved enable 1,4‐hetero‐difunctionalization, which δ‐fluoro‐alcohol amine derivatives forged in operation. protocol compatible with variety nucleophiles including fluoride, nitriles, carboxylic acids, alcohols even water thereby allowing products, stereocenter bearing both C(sp 3 )−F )−CF groups, generated rapidly. Scalability (up mmol), facile post‐reaction modifications are demonstrated underscore the utility method expanding organofluorine chemical space.

Language: Английский

Citations

1
Multigram-Scale Synthesis of a gem-Difluoro-Substituted 4,5,6,7-Tetrahydrobenzo[c]thiophen-4-one Heterocycle via Oxidative Chlorination and Radical Smiles Rearrangement DOI
Craig Jamieson, Martyn C. Henry,

Jack Q. Anderson

et al.

Synlett, Journal Year: 2023, Volume and Issue: unknown

Published: Aug. 14, 2023

Abstract We report an optimized synthetic route towards a functionalized 4,5,6,7-tetrahydrobenzo[c]thiophene heterocycle bearing gem-difluoromethylene moiety in 4 steps with overall yield of 43%. The CF2 fragment was incorporated using building block approach, by coupling appropriate fluorinated alcohol C-3 sulfonyl chloride, synthesized via oxidative chlorination exocyclic benzyl thioether. Visible-light-mediated Smiles rearrangement the resulting fluorosulfonate ester then furnishes desired thiophene scaffold.

Language: Английский

Citations

0