tert‐Butyl as a Functional Group: Non‐Directed Catalytic Hydroxylation of Sterically Congested Primary C−H Bonds DOI Creative Commons
Siu‐Chung Chan, Andrea Palone, Massimo Bietti

et al.

Angewandte Chemie, Journal Year: 2024, Volume and Issue: 136(28)

Published: May 1, 2024

Abstract The tert ‐butyl group is a common aliphatic motif extensively employed to implement steric congestion and conformational rigidity in organic organometallic molecules. Because of the combination high bond dissociation energy (~100 kcal mol −1 ) limited accessibility, absence directing groups, neither radical nor approaches are effective for chemical modification C−H bonds. Herein we overcome these limits by employing highly electrophilic manganese catalyst, [Mn( CF3 bpeb)(OTf) 2 ], that operates strong hydrogen donor solvent nonafluoro‐ alcohol (NFTBA) catalytically activates peroxide generate powerful manganese‐oxo species effectively oxidizes Leveraging on interplay steric, electronic, medium torsional effects, site‐selective product chemoselective hydroxylation accomplished with broad reaction scope, delivering primary alcohols as largely dominant products preparative yields. Late‐stage at sites demonstrated 6 densely functionalized molecules pharmaceutical interest. This work uncovers novel disconnection approach, harnessing potential functional strategic synthetic planning complex molecular architectures.

Language: Английский

Atomic-Level Regulation of Mn Monovacancies of 2D-Mn2O3 for High-Efficient Catalytic Diesel Oxidation DOI
Lei Chen, Huixin Zhang, Yang‐wen Wu

et al.

ACS Catalysis, Journal Year: 2025, Volume and Issue: unknown, P. 6226 - 6238

Published: April 2, 2025

Language: Английский

Citations

0
Leveraging electron distribution reconstruction of spinel MnCo2O4 hollow microflowers for the aerobic oxidation of limonene DOI
Jiangyong Liu, Chennan Wang, Bing Liu

et al.

Applied Catalysis A General, Journal Year: 2025, Volume and Issue: unknown, P. 120331 - 120331

Published: May 1, 2025

Language: Английский

Citations

0
tert‐Butyl as a Functional Group: Non‐Directed Catalytic Hydroxylation of Sterically Congested Primary C−H Bonds DOI Creative Commons
Siu‐Chung Chan, Andrea Palone, Massimo Bietti

et al.

Angewandte Chemie International Edition, Journal Year: 2024, Volume and Issue: 63(28)

Published: May 1, 2024

Abstract The tert ‐butyl group is a common aliphatic motif extensively employed to implement steric congestion and conformational rigidity in organic organometallic molecules. Because of the combination high bond dissociation energy (~100 kcal mol −1 ) limited accessibility, absence directing groups, neither radical nor approaches are effective for chemical modification C−H bonds. Herein we overcome these limits by employing highly electrophilic manganese catalyst, [Mn( CF3 bpeb)(OTf) 2 ], that operates strong hydrogen donor solvent nonafluoro‐ alcohol (NFTBA) catalytically activates peroxide generate powerful manganese‐oxo species effectively oxidizes Leveraging on interplay steric, electronic, medium torsional effects, site‐selective product chemoselective hydroxylation accomplished with broad reaction scope, delivering primary alcohols as largely dominant products preparative yields. Late‐stage at sites demonstrated 6 densely functionalized molecules pharmaceutical interest. This work uncovers novel disconnection approach, harnessing potential functional strategic synthetic planning complex molecular architectures.

Language: Английский

Citations

2
Palladium catalyzed C(sp3)–H trifluoroethoxylation DOI
Dmitry P. Lubov,

Konstantin S. Ivanov,

Andrey A. Nefedov

et al.

Journal of Catalysis, Journal Year: 2024, Volume and Issue: 435, P. 115563 - 115563

Published: May 18, 2024

Language: Английский

Citations

1
Selective C–H Oxidation Enabled by Manganese Catalysis DOI
Mark Lautens, Colton E. Johnson

Synfacts, Journal Year: 2024, Volume and Issue: 20(06), P. 0615 - 0615

Published: May 14, 2024

Key words oxidation - C–H functionalization biomimetic catalysis base–metal

Language: Английский

Citations

0
Activation of hydrogen peroxide with biologically inspired non-heme iron and manganese catalysts: From simple molecular complexes to modification of the second coordination sphere DOI
Laia Vicens, Miguel Costas

Advances in inorganic chemistry, Journal Year: 2024, Volume and Issue: unknown, P. 1 - 19

Published: Jan. 1, 2024

Language: Английский

Citations

0
tert‐Butyl as a Functional Group: Non‐Directed Catalytic Hydroxylation of Sterically Congested Primary C−H Bonds DOI Creative Commons
Siu‐Chung Chan, Andrea Palone, Massimo Bietti

et al.

Angewandte Chemie, Journal Year: 2024, Volume and Issue: 136(28)

Published: May 1, 2024

Abstract The tert ‐butyl group is a common aliphatic motif extensively employed to implement steric congestion and conformational rigidity in organic organometallic molecules. Because of the combination high bond dissociation energy (~100 kcal mol −1 ) limited accessibility, absence directing groups, neither radical nor approaches are effective for chemical modification C−H bonds. Herein we overcome these limits by employing highly electrophilic manganese catalyst, [Mn( CF3 bpeb)(OTf) 2 ], that operates strong hydrogen donor solvent nonafluoro‐ alcohol (NFTBA) catalytically activates peroxide generate powerful manganese‐oxo species effectively oxidizes Leveraging on interplay steric, electronic, medium torsional effects, site‐selective product chemoselective hydroxylation accomplished with broad reaction scope, delivering primary alcohols as largely dominant products preparative yields. Late‐stage at sites demonstrated 6 densely functionalized molecules pharmaceutical interest. This work uncovers novel disconnection approach, harnessing potential functional strategic synthetic planning complex molecular architectures.

Language: Английский

Citations

0