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Dual Catalysis. Single-electron Transmetalation in Organoboron Cross-Coupling by photoredox/nickel Dual Catalysis

Dual Catalysis. Single-electron Transmetalation in Organoboron Cross-Coupling by photoredox/nickel Dual Catalysis

John C Tellis, David N Primer, Gary A Molander

Science. 2014 Jul 25;345(6195):433-6.

PMID: 24903560

Abstract:

The routine application of C(sp3)-hybridized nucleophiles in cross-coupling reactions remains an unsolved challenge in organic chemistry. The sluggish transmetalation rates observed for the preferred organoboron reagents in such transformations are a consequence of the two-electron mechanism underlying the standard catalytic approach. We describe a mechanistically distinct single-electron transfer-based strategy for the activation of organoboron reagents toward transmetalation that exhibits complementary reactivity patterns. Application of an iridium photoredox catalyst in tandem with a nickel catalyst effects the cross-coupling of potassium alkoxyalkyl- and benzyltrifluoroborates with an array of aryl bromides under exceptionally mild conditions (visible light, ambient temperature, no strong base). The transformation has been extended to the asymmetric and stereoconvergent cross-coupling of a secondary benzyltrifluoroborate.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP329976730	Potassium benzyltrifluoroborate		329976-73-0	Price

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