α‐Arylation/Heteroarylation of Chiral α‐Aminomethyltrifluoroborates by Synergistic Iridium Photoredox/Nickel Cross‐Coupling Catalysis

Khatib, Mirna El; Serafim, Ricardo Augusto Massarico; Molander, Gary A.

doi:10.1002/anie.201506147

Cited by 139 publications

(57 citation statements)

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“…This strategy has been applied to benzylic, 279,281 secondary alkyl, 282 alkoxymethyl, 283,284 and α-amino 285 boron nucleophiles. Notably, the mild conditions utilized for the photooxidation of the trifluoroborate salts do not affect other organoboron species.…”

Section: Photoinduced Electron Transfermentioning

confidence: 99%

Dual Catalysis Strategies in Photochemical Synthesis

2016

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The interaction between an electronically excited photocatalyst and an organic molecule can result in the genertion of a diverse array of reactive intermediates that can be manipulated in a variety of ways to result in synthetically useful bond constructions. This Review summarizes dual-catalyst strategies that have been applied to synthetic photochemistry. Mechanistically distinct modes of photocatalysis are discussed, including photoinduced electron transfer, hydrogen atom transfer, and energy transfer. We focus upon the cooperative interactions of photocatalysts with redox mediators, Lewis and Brønsted acids, organocatalysts, enzymes, and transition metal complexes.

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Section: Photoinduced Electron Transfermentioning

confidence: 99%

Dual Catalysis Strategies in Photochemical Synthesis

2016

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“…Chiral a-aminomethyltrifluoroborates were also tested in the cross-coupling reaction with aryl-and heteroaryl bromides, using synergistic photoredox/Ni dual catalysis [23]. The best set of conditions was established using [Ir(dF(CF 3 )ppy) 2 (bpy)](PF 6 ) as the photocatalyst, Ni(NO 3 ) 2 Á6H 2 O/bioxazole as the cross-coupling precatalyst, and 2,6-lutidine as an additive, with irradiation from a 26-W CFL at room temperature to promote the reaction (Scheme 12).…”

Section: Cross-coupling With Organotrifluoroboratesmentioning

confidence: 99%

Photoredox Catalysis in Nickel-Catalyzed Cross-Coupling

Cavalcanti

Molander

2016

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The traditional transition metal-catalyzed cross-coupling reaction, although well suited for C(sp2)-C(sp2) cross-coupling, has proven less amenable toward coupling of C(sp3)-hybridized centers, particularly using functional group tolerant reagents and reaction conditions. The development of photoredox/Ni dual catalytic methods for cross-coupling has opened new vistas for the construction of carbon-carbon bonds at C(sp3)-hybridized centers. In this chapter, a general outline of the features of such processes is detailed.

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“…Due to their high stability and storability wide application was achieved. 27 In a Ni transition metal merged Ir photocatalyzed coupled system, a wide variety of (hetero)aryl bromides were coupled with subtituated benzyl BF 3 K salts, 26,28 secondary alkyl trifluoroboates, 29 α-alkoxymethyltrifluoroborates, 30 Bocprotected N-trifluoroboratomethyl amino acids 31 and aryl or aralkyl acyl chlorides with α-alkoxymethyltrifluoroborates. 32 In 2016, the synthesis of 1,1-diaryl-2,2,2-trifluoroethanes (16) were investigated by Molander and his co-workers (Figure 6).…”

Section: Alkylations With Rbf 3 K Salts By Photoredox Cross-couplingmentioning

confidence: 99%