Stereodefined rhodium-catalysed 1,4-H/D delivery for modular syntheses and deuterium integration

Synthesis of Trifluoromethyl-Substituted Allenols via Catalytic Trifluoromethylbenzoxylation of 1,3-Enynes

“…The trifluoromethyl (CF 3 ) group functions as an excellent bioisostere of the methyl group in medicinal chemistry, owing to its potential to improve the metabolic stability, bioavailability, and cellular membrane permeability of molecules . Accordingly, incorporation of a trifluoromethyl group into molecular skeletons has attracted significant interest for organic synthesis. − Allenol is a versatile synthon that undergoes diverse transformations, including eliminations, substitutions, and rearrangements (Figure A) . Therefore, a CF 3 -substituted allenol could be a multipurpose building block that allows expedited access to CF 3 -substituted compounds with diverse molecular skeletons. , …”

[Cp*RhCl2]2catalyzed three-component coupling cyclization of 2,3-allenoic acids with 2,3-allenols in the presence of Cu(OAc)2·H2O

“…Based on these experimental results and the literature, 3–5 two mechanisms were proposed, as shown in Scheme 4. First, [Cp*RhCl 2 ] 2 would undergo ligand exchange to afford Cp*RhOAc 2 .…”

Transition-metal-free silylboronate-mediated cross-couplings of organic fluorides with amines

“…Isotope labeling is generally critical in medicinal chemistry as the C-D bonds are more stable than C-H bonds 50 . Therefore, incorporating deuterated N-methyl (N-CD 3 ) moieties into pharmaceuticals should improve the pharmacodynamic properties [51][52][53][54][55][56] . Considering this aspect, several representative fluorocontaining derivatives of bioactive molecules, 1ad-1ag, were reacted with deuterated N-methylaniline d 3 −3a under standard conditions.…”