Final published version
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Research output: Contribution to Journal/Magazine › Journal article › peer-review
Research output: Contribution to Journal/Magazine › Journal article › peer-review
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TY - JOUR
T1 - Iron-Catalysed C(sp2)-H Borylation with Expanded Functional Group Tolerance†
AU - Britton, Luke
AU - Docherty, Jamie H.
AU - Nichol, Gary S.
AU - Dominey, Andrew P.
AU - Thomas, Stephen P.
PY - 2022/12/15
Y1 - 2022/12/15
N2 - Arene C(sp2)-H bond borylation offers direct and efficient access to aryl boronic esters. Using in situ catalyst activation and photoirradiation, the iron-catalysed C(sp2)-H borylation reaction of carboarenes, pyrroles, and indoles has been developed using only bench-stable pre-catalysts and reagents. Good functional group tolerance was observed including those not reported using previous methods (ArNH2, ArOH, ArSiR3, ArP(O)(OR)2, ArC(O)NR2). Mechanistic studies revealed iron-catalysed reductive deoxygenation, C—F protodefluorination, and a demethylation of aryl methyl ethers by C—O sigma bond hydroboration.
AB - Arene C(sp2)-H bond borylation offers direct and efficient access to aryl boronic esters. Using in situ catalyst activation and photoirradiation, the iron-catalysed C(sp2)-H borylation reaction of carboarenes, pyrroles, and indoles has been developed using only bench-stable pre-catalysts and reagents. Good functional group tolerance was observed including those not reported using previous methods (ArNH2, ArOH, ArSiR3, ArP(O)(OR)2, ArC(O)NR2). Mechanistic studies revealed iron-catalysed reductive deoxygenation, C—F protodefluorination, and a demethylation of aryl methyl ethers by C—O sigma bond hydroboration.
KW - Boron
KW - C—H borylation
KW - Earth-abundant
KW - Iron
KW - Photochemistry
U2 - 10.1002/cjoc.202200465
DO - 10.1002/cjoc.202200465
M3 - Journal article
AN - SCOPUS:85139991489
VL - 40
SP - 2875
EP - 2881
JO - Chinese Journal of Chemistry
JF - Chinese Journal of Chemistry
SN - 1001-604X
IS - 24
ER -