Rhodium (i)-catalyzed 1, 4-conjugate arylation toward β-fluoroalkylated electron-deficient alkenes: a new entry to a construction of a tertiary carbon center possessing …

A Morigaki, T Tanaka, T Miyabe, T Ishihara…

Index: Morigaki, Atsunori; Tanaka, Tomoo; Miyabe, Tomotsugu; Ishihara, Takashi; Konno, Tsutomu Organic and Biomolecular Chemistry, 2013 , vol. 11, # 4 p. 586 - 595

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Citation Number: 23

Abstract

Treatment of β-fluoroalkylated-α, β-unsaturated ketones with 1.2 equiv. of various arylboronic acids in the presence of 5 mol% of [Rh (COD) 2] BF4 and 6 mol% of (S)-BINAP in toluene/H2O (v/v= 4/1) at the reflux temperature for 3 h gave the corresponding Michael adducts in high yields with over 90% enantioselectivity. Though other electron-deficient alkenes, such as vinylsulfone and vinylphosphonate, were found to be much less reactive ...