Photoredox Cross-Coupling: Ir/Ni Dual Catalysis for the Synthesis of Benzylic Ethers
Single-electron transmetalation has emerged as an enabling paradigm for the cross-coupling of Csp3 hybridized organotrifluoroborates. Cross-coupling of α-alkoxymethyltrifluoroborates with aryl and heteroaryl bromides has been demonstrated by employing dual catalysis with a combination of an iridium photoredox catalyst and a Ni cross-coupling catalyst. The resulting method enables the alkoxymethylation of diverse (hetero)arenes under mild, room-temperature conditions. (Chemical Equation Presented).
Karakaya, Idris,Primer, David N.,Molander, Gary A.
supporting information
p. 3294 - 3297
(2015/07/15)
Flow synthesis of annulated 5-aryl-substituted pyridines by tandem intramolecular inverse-electron-demand hetero-/retro-Diels-Alder reaction
5-Aryl-substituted annulated pyridines can be accessed directly from the corresponding acetylene substituted pyrimidines through an intramolecular inverse-electron-demand hetero-/retro-Diels-Alder (ihDA/rDA) reaction cascade carried out in continuous flow. Exploiting this new process, a series of cycloalka[c]pyridines that represent useful building blocks for medicinal chemistry were prepared in good to excellent yields with short processing times (45 min). Importantly, utilizing the ability to superheat solvents in flow permits the replacement of typically employed high boiling solvents (e.g.; nitrobenzene or chlorobenzene) with toluene.
Martin, Rainer E.,Lenz, Mario,Alzieu, Thibaut,Aebi, Johannes D.,Forzy, Liliane
supporting information
p. 6703 - 6707
(2013/11/19)
SYNTHESIS OF 1,3-DIHYDROFUROPYRIDINES AND 5,7-DIHYDROFUROPYRIDINES BY INTRAMOLECULAR DIELS-ALDER REACTIONS OF PYRIMIDINES. INVESTIGATION OF THE EFFECT OF STERIC INTERACTIONS ON THE REACTION RATE
Several 2- and 5-propynyloxymethylpyrimidines were synthesized and their intramolecular Diels-Alder reaction was studied.The products of the reaction were 5,7-dihydrofuropyridines and 1,3-dihydrofuropyridines, respectively.Introduction of on
Frissen, A. E.,Marcelis, A. T. M.,Buurman, D. G,Pollmann, C. A. M.,Plas, H. C. van der
p. 5611 - 5620
(2007/10/02)
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