Journal
ORGANIC CHEMISTRY FRONTIERS
Volume 8, Issue 21, Pages 5975-5981Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/d1qo00895a
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Funding
- National Science Foundation of China [21861030]
- Collaborative Innovation Center for Water Environmental Security of Inner Mongolia Autonomous Region [XTCX003]
- Science and Technology Program of Inner Mongolia Autonomous Region [2020PT0003]
- Nature Science Foundation of Inner Mongolia [2020LH02010]
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A novel method for achieving regiodivergent C(sp(3))-H and C(sp(2))-H polyfluoroalkoxylation in the o-methyl benzaldehyde framework by altering the transient directing group is disclosed. The selectivity is proposed to be governed by the size of the palladacycle generated from Pd-chelation with different transient directing groups. This approach provides a new avenue for controlled regiodivergent C(sp(3))-H and C(sp(2))-H functionalization reactions.
A novel method for achieving regiodivergent C(sp(3))-H and C(sp(2))-H polyfluoroalkoxylation in the o-methyl benzaldehyde framework by altering the transient directing group is disclosed. Using palladium as the catalyst and [F+] reagents as bystanding oxidants, various regioisomeric polyfluoroalkoxylated benzaldehydes were prepared. It is proposed that the selectivity is governed by the size of the palladacycle which is generated from Pd-chelation with different transient directing groups and helps in harnessing palladium with the benzyl C(sp(3))-H or C(sp(2))-H bonds of o-methyl benzaldehydes. These findings provide an avenue for controlled regiodivergent C(sp(3))-H and C(sp(2))-H functionalization reactions.
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