Enantioselective Decarboxylative Arylation of α-Amino Acids via the Merger of Photoredox and Nickel Catalysis

Zuo, Zhiwei; Cong, Huan; Li, Wei; Choi, Jun Won; Fu, Gregory C.; MacMillan, David W. C.

doi:10.1021/jacs.5b13211

Cited by 466 publications

(225 citation statements)

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“…The electrondeficient arenes appear to be more effective for high ees. The coupling with iodobenzene only produced 66 % ee and 64 % yield [82]. A mechanism illustrated in Scheme 18 may operate.…”

Section: Enantioselective C(sp 3 )-C(sp 2 ) Bond Formationmentioning

confidence: 99%

Nickel-Catalyzed Reductive Couplings

2016

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The Ni-catalyzed reductive coupling of alkyl/aryl with other electrophiles has evolved to be an important protocol for the construction of C-C bonds. This chapter first emphasizes the recent progress on the Ni-catalyzed alkylation, arylation/vinylation, and acylation of alkyl electrophiles. A brief overview of CO2 fixation is also addressed. The chemoselectivity between the electrophiles and the reactivity of the alkyl substrates will be detailed on the basis of different Ni-catalyzed conditions and mechanistic perspective. The asymmetric formation of C(sp(3))-C(sp(2)) bonds arising from activated alkyl halides is next depicted followed by allylic carbonylation. Finally, the coupling of aryl halides with other C(sp(2))-electrophiles is detailed at the end of this chapter.

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Section: Enantioselective C(sp 3 )-C(sp 2 ) Bond Formationmentioning

confidence: 99%

Nickel-Catalyzed Reductive Couplings

2016

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“…An enantioselective version of the dual photoredox/Ni catalyzed crosscoupling of commercially available a-amino acids and aryl bromides was also sought [47]. Under conditions very similar to those developed for the achiral transformation but using a chiral ligand, it was possible to synthesize benzylic amines in good to excellent yields and ees up to 92 % (Scheme 32).…”

Section: Scheme 26mentioning

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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“…20 In the following year, the scope was expanded to the coupling of α-oxo acids and alkyl acids with vinyl haides, 21 and subsequently a new reaction was described for enantioselective arylation of α-amino acids. 22 In 2015, MacMillan presented a Ni-Ir dual setup for decarboxylative coupling of aryl halides (10: I, Br) with 2 equivalents of ketocarboxylic acids(11) (Figure 5). 23 Similarly to the previously mentioned synergistic dual catalytic mechanism, photo-generated acyl radical adds to the Ni(0) complex.…”

Section: Decarboxylative Photoredox Cross-coupling Reactionsmentioning

confidence: 99%