Enantioselective\nIntermolecular Benzylic C–H\nAmination under Chiral Paddle-Wheel Diruthenium Catalysis

A catalytic asymmetric intermolecular benzylic C–H\namination\nwas achieved under paddle-wheel diruthenium catalysis. A chiral diruthenium\ncatalyst incorporating (<i>S</i>)-TPPTTL (tetraphenylphthaloyl-(<i>S</i>)-<i>tert</i>-leucine) ligand exhibited notable\nenantioselectivity, and aminated products were obtained with up to\n99% ee. Unique chemoselectivity of the chiral diruthenium catalyst\nwas also found for allylbenzene and alkyl-naphthalene substrates,\ndemonstrating the complementary synthetic utility of chiral paddle-wheel\nRu(II)–Ru(III) catalysts to Rh(II) counterparts.

Publication Details

Journal
Figshare
Published
2024-12-20
DOI
https://doi.org/10.1021/acscatal.4c06504.s002
Primary Topic
Catalytic C–H Functionalization Methods
Type
article
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article

Enantioselective\nIntermolecular Benzylic C–H\nAmination under Chiral Paddle-Wheel Diruthenium Catalysis

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Catalytic C–H Functionalization Methods
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Enantioselective\nIntermolecular Benzylic C–H\nAmination under Chiral Paddle-Wheel Diruthenium Catalysis

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Abstract

A catalytic asymmetric intermolecular benzylic C–H\namination\nwas achieved under paddle-wheel diruthenium catalysis. A chiral diruthenium\ncatalyst incorporating (<i>S</i>)-TPPTTL (tetraphenylphthaloyl-(<i>S</i>)-<i>tert</i>-leucine) ligand exhibited notable\nenantioselectivity, and aminated products were obtained with up to\n99% ee. Unique chemoselectivity of the chiral diruthenium catalyst\nwas also found for allylbenzene and alkyl-naphthalene substrates,\ndemonstrating the complementary synthetic utility of chiral paddle-wheel\nRu(II)–Ru(III) catalysts to Rh(II) counterparts.

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Catalytic C–H Functionalization Methods
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Enantioselective\nIntermolecular Benzylic C–H\nAmination under Chiral Paddle-Wheel Diruthenium Catalysis · Figshare (2024) | TGRS Research Map | TGRS