Regiochemical Switching in Ir-Catalyzed C-H Borylation by Altering Ligand Loadings of N,B-Type Diboron Species.
| Autor: | O'Connell AC; Department of Chemistry, Michigan State University, 578 South Shaw Lane, East Lansing 48824-1322, Michigan United States., Mansour PA; Department of Chemistry, Michigan State University, 578 South Shaw Lane, East Lansing 48824-1322, Michigan United States., Maleczka RE Jr; Department of Chemistry, Michigan State University, 578 South Shaw Lane, East Lansing 48824-1322, Michigan United States., Smith MR 3rd; Department of Chemistry, Michigan State University, 578 South Shaw Lane, East Lansing 48824-1322, Michigan United States. |
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| Jazyk: | angličtina |
| Zdroj: | Organic letters [Org Lett] 2023 Nov 17; Vol. 25 (45), pp. 8057-8061. Date of Electronic Publication: 2023 Nov 08. |
| DOI: | 10.1021/acs.orglett.3c02760 |
| Abstrakt: | Traditional reaction conditions in Ir-catalyzed C-H borylation consist of a 2:1 ligand to Ir metal ratio, affording C(sp 2 )-H borylation at the least sterically hindered position. We found that lowering the ligand to metal ratio of a N,B-type diboron (BB) preligand in respect to the Ir I precatalyst to 0.5:1 affords the chelate controlled ortho product. Switching from steric-directed to chelate-directed products is shown for various substituted arenes and (hetero)arenes containing Lewis-basic functionalities. This work offers the first example of obtaining complementary regioisomers as the major product by altering the ligand loading in CHB. |
| Databáze: | MEDLINE |
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