TY - JOUR

T1 - 4-Ethoxy-1,1,1-trifluoro-3-buten-2-one (ETFBO), a Versatile Precursor for Trifluoromethyl-Substituted Heteroarenes

T2 - A Short Synthesis of Celebrex ® (Celecoxib)

AU - Sommer, Heiko

AU - Braun, Max

AU - Schröder, Benjamin

AU - Kirschning, Andreas

N1 - Funding information: The authors are indebted to Dr. R. D. Shannon of E. I. du Pont de Nemours and Co., U.S.A., who kindly furnished the electrolyte samples and thank the Consiglio Nazionale delle Ricerche for the financial support.

PY - 2017/8/22

Y1 - 2017/8/22

N2 - 4-Ethoxy-1,1,1-trifluoro-3-buten-2-one (ETFBO) serves as a trifluoromethyl-containing building block for the preparation of trifluoromethyl-substituted thiophenes, furans, pyrrols, and piperazines. Key steps are an addition-elimination reaction to ETFBO followed by the thiazolium-catalyzed Stetter reaction. The scope of this chemistry was demonstrated in a new synthetic approach towards the COX-2 selective, nonsteroidal anti-inflammatory drug Celebrex ® (celecoxib).

AB - 4-Ethoxy-1,1,1-trifluoro-3-buten-2-one (ETFBO) serves as a trifluoromethyl-containing building block for the preparation of trifluoromethyl-substituted thiophenes, furans, pyrrols, and piperazines. Key steps are an addition-elimination reaction to ETFBO followed by the thiazolium-catalyzed Stetter reaction. The scope of this chemistry was demonstrated in a new synthetic approach towards the COX-2 selective, nonsteroidal anti-inflammatory drug Celebrex ® (celecoxib).

KW - antiinflammation

KW - heteroarenes

KW - organocatalysis

KW - Stetter reaction

KW - trifluoromethyl group

UR - http://www.scopus.com/inward/record.url?scp=85028323009&partnerID=8YFLogxK

U2 - 10.1055/s-0036-1589097

DO - 10.1055/s-0036-1589097

M3 - Article

AN - SCOPUS:85028323009

VL - 29

SP - 121

EP - 125

JO - Synlett

JF - Synlett

SN - 0936-5214

IS - 1

M1 - st-2017-b0101-l

ER -