Chemical synthesis study demonstrates catalyst-controlled positional-selective C–H alkenylation of isoxazoles, suggesting a modular pathway to densely substituted pyrroles.
High levels of catalyst control are demonstrated in determining the positional selectivity in C–H alkenylation of isoxazoles. A cationic rhodium-mediated, strong-directing group promotes C( sp 2 )-H activation at the proximal aryl ring whereas, the palladium-mediated electrophilic metallation leads to the C( sp 2 )-H activation at the distal position of the directing group. Synthetic elaboration of this C–H alkenylation product via ruthenium and copper co-catalysis leads to an efficient method for the assembly of densely substituted pyrroles.
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Kumar et al. (2019) studied this question.
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