1 3
Topics in Current Chemistry (2018) 376:46
conversion of 1-methoxy-4-(prop-2-yn-1-yloxy)benzene into a 95:5 mixture of
59a and 59b was attained in 40 min. The recycled cartridge was also tested in the
cycloisomerization reaction of 4-methyl-N-(3-methylbut-2-en-1-yl)-N-(prop-2yn-1-yl)benzenesulfonamide, observing complete conversion of the substrate into
a 4:1 mixture of compounds 60a and 60b in 20 min.
Liu and Cui reported the use of a manganese-containing metal–organic
framework (MOF) 61 in asymmetric Friedel–Crafts alkylations of indoles
under flow conditions [70]. A chiral MOF was prepared from enantiopure
phosphono-carboxylate ligand (H 5 L
1
) deriving from 1,1′-biphenol functionalized with 3,5bis(trifluoromethyl)-phenyl substituents at the 3,3′ position. The
CF 3 -containing MOF demonstrated excellent selectivity and recyclability,
according high yields and enantioselectivities in the alkylations of indoles with
a range of ketoesters or nitroalkenes (Scheme 27). The outstanding recyclability of 61 allowed for its use in a stainless-steel packed-bed flow reactor. The
reactions of N-methylindole and α-keto esters under continuous flow conditions
furnished adducts 62a–c in 89–92% yield with 95:5–97:3 enantiomeric ratios.
In the flow reactor, 61 gave a slight increase in catalytic activity compared with
Scheme 25 Continuous flow hydrosilylation reaction of alkyne and PhSiH 3 using supported phosphinic
ligand
Scheme 26 Hydroarylation and cycloisomerization carried out sequentially under continuous flow conditions using supported catalyst 58
53
Reprinted from the journal
Topics in Current Chemistry (2018) 376:46
conversion of 1-methoxy-4-(prop-2-yn-1-yloxy)benzene into a 95:5 mixture of
59a and 59b was attained in 40 min. The recycled cartridge was also tested in the
cycloisomerization reaction of 4-methyl-N-(3-methylbut-2-en-1-yl)-N-(prop-2yn-1-yl)benzenesulfonamide, observing complete conversion of the substrate into
a 4:1 mixture of compounds 60a and 60b in 20 min.
Liu and Cui reported the use of a manganese-containing metal–organic
framework (MOF) 61 in asymmetric Friedel–Crafts alkylations of indoles
under flow conditions [70]. A chiral MOF was prepared from enantiopure
phosphono-carboxylate ligand (H 5 L
1
) deriving from 1,1′-biphenol functionalized with 3,5bis(trifluoromethyl)-phenyl substituents at the 3,3′ position. The
CF 3 -containing MOF demonstrated excellent selectivity and recyclability,
according high yields and enantioselectivities in the alkylations of indoles with
a range of ketoesters or nitroalkenes (Scheme 27). The outstanding recyclability of 61 allowed for its use in a stainless-steel packed-bed flow reactor. The
reactions of N-methylindole and α-keto esters under continuous flow conditions
furnished adducts 62a–c in 89–92% yield with 95:5–97:3 enantiomeric ratios.
In the flow reactor, 61 gave a slight increase in catalytic activity compared with
Scheme 25 Continuous flow hydrosilylation reaction of alkyne and PhSiH 3 using supported phosphinic
ligand
Scheme 26 Hydroarylation and cycloisomerization carried out sequentially under continuous flow conditions using supported catalyst 58
53
Reprinted from the journal