Palladium Aminopyridine Complexes Catalyzed Selective Benzylic C–H Oxidations with Peracetic Acid
Full article
| Common |
Language:
Английский,
Genre:
Full article,
Status:
Published,
Source type:
Original
|
| Journal |
Dalton Transactions
ISSN: 1477-9226
, E-ISSN: 1477-9234
|
| Output data |
Year: 2020,
Volume: 49,
Number: 32,
Pages: 11150-11156
Pages count
: 7
DOI:
10.1039/d0dt02247k
|
| Tags |
HYDROGEN-ATOM ABSTRACTION; ALKANE HYDROXYLATION; KINETIC RESOLUTION; ALCOHOLS; MANGANESE; BOND; HYDROCARBONS; FUNCTIONALIZATION; AUTOXIDATION; ARYLALKANES |
| Authors |
Lubov Dmitry P.
1,2
,
Lyakin Oleg Yu.
1,2
,
Samsonenko Denis G.
2,3
,
Rybalova Tatyana V.
2,4
,
Talsi Evgenii P.
1,2
,
Bryliakov Konstantin P.
1,2
|
| Affiliations |
| 1 |
Boreskov Institute of Catalysis, Pr. Lavrentieva 5, Novosibirsk 630090, Russia
|
| 2 |
Novosibirsk State University, Pirogova 1, Novosibirsk 630090, Russia
|
| 3 |
Nikolaev Institute of Inorganic Chemistry, Pr. Lavrentieva 3, Novosibirsk 630090, Russia
|
| 4 |
Vorozhtsov Novosibirsk Institute of Organic Chemistry, Pr. Lavrentieva 9, Novosibirsk 630090, Russia
|
|
Funding (1)
|
1
|
Russian Science Foundation
|
17-13-01117
|
Four palladium(II) complexes with tripodal ligands of the tpa family (tpa = tris(2-pyridylmethyl)amine) have been synthesized and X-ray characterized. These complexes efficiently catalyze benzylic C–H oxidation of various substrates with peracetic acid, affording the corresponding ketones in high yields (up to 100%), at <1 mol% catalyst loadings. Complex [(tpa)Pd(OAc)](PF6) with the least sterically demanding ligand tpa demonstrates the highest substrate conversions and ketone selectivities. Preliminary mechanistic data provide evidence in favor of metal complex-mediated rate-limiting benzylic C–H bond cleavage by an electron-deficient oxidant.