Iron-catalysed enantioconvergent Suzuki–Miyaura cross-coupling to afford enantioenriched 1,1-diarylalkanes

Tyrol, Chet; Yone, Nang; Gallin, Connor F.; Byers, Jeffery A.

doi:10.1039/d0cc05003b

Cited by 37 publications

(31 citation statements)

References 40 publications

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“…This work provided a proof-of-concept towards the use of vinylcyclopropanes as useful 1,5-synthons in asymmetric Fe-catalyzed cross-coupling reactions. Although poor enantioinduction was observed, several Fe-catalyzed non-sequential cross-coupling protocols have been established with yields and enantioselectivity rivaling Pd-catalyzed reactions [ 64 – 65 ]. Mechanistically, these reactions differ by not including a π-system which allows for propagation of reaction.…”

Section: Reviewmentioning

confidence: 99%

Iron-catalyzed domino coupling reactions of π-systems

Pounder¹,

Tam²

2021

Beilstein J. Org. Chem.

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The development of environmentally benign, inexpensive, and earth-abundant metal catalysts is desirable from both an ecological and economic standpoint. Certainly, in the past couple decades, iron has become a key player in the development of sustainable coupling chemistry and has become an indispensable tool in organic synthesis. Over the last ten years, organic chemistry has witnessed substantial improvements in efficient synthesis because of domino reactions. These protocols are more atom-economic, produce less waste, and demand less time compared to a classical stepwise reaction. Although iron-catalyzed domino reactions require a mindset that differs from the more routine noble-metal, homogenous iron catalysis they bear the chance to enable coupling reactions that rival that of noble-metal-catalysis. This review provides an overview of iron-catalyzed domino coupling reactions of π-systems. The classifications and reactivity paradigms examined should assist readers and provide guidance for the design of novel domino reactions.

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Section: Reviewmentioning

confidence: 99%

Iron-catalyzed domino coupling reactions of π-systems

Pounder¹,

Tam²

2021

Beilstein J. Org. Chem.

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“…In 2020, Tyrol et al reported an iron-catalyzed enantioselective Suzuki-Miyaura cross-coupling in the presence of iron and a chiral cyanobis(oxazoline) complex L4, affording optically active 1,1-diarylalkanes in low to excellent yields (35-90 %) and with moderate to excellent enantioselectivities (er = 73 : 27-99 : 1) (Scheme 6). [10] Scheme 4. Iron-catalyzed enantioselective couplings of alkyl bromides and lithium arylborates.…”

Section: Iron-catalyzed Enantioselective Cross-couplingsmentioning

confidence: 99%

Enantioselective Cross‐couplings between Halide Derivatives and Organometallics by Using Iron and Cobalt Catalysts: Formation of C−C Bonds

Shu

Cossy

2021

Chemistry A European J

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“…The major byproduct observed in these reactions was alkane 5 that results from protodehalogenation of the electrophile. 29 As we have seen previously, 5,30,31 using presynthesized 2 was essential for obtaining high yields of cross-coupled product. Lower yields were obtained when attempting to form the complex in situ by mixing FeCl2 with the b-dekitiminate ligand (entry 2).…”

mentioning

confidence: 92%

“…While mechanistic investigations are beyond the scope of this study, our current working mechanistic hypothesis is a bimetallic mechanism similar to what we have proposed previously for alkyl-aryl Suzuki-Miyaura cross-coupling reactions (Scheme 3). 5,31 In this bimetallic mechanism, iron(II) halide I undergoes salt metathesis with the lithium amide to form iron(II) amide II. This intermediate is poised for transmetalation with the alkylborane to form iron(II) alkyl complex III.…”

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confidence: 99%

A Broadly Applicable Alkyl-Alkyl Suzuki-Miyaura Cross-Coupling Reaction Catalyzed by an Iron-Based Complex

Tyrol

Byers

2021

Preprint

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An iron-based catalyst for the Suzuki-Miyaura reaction between two sp3-hybridized substrates has been developed for a broad range of unactivated alkyl halides and alkyl boranes. Key to success was using a Cs-symmetric beta-diketiminate ligand that contained a tert-butyl and trifluoromethyl functionalized backbone. The breadth of the cross-coupling reaction was demonstrated with high yields of cross-coupled products observed from reactions using primary and secondary alkyl bromides as well as primary alkyl boranes and even some secondary alkyl boranes. Complementary methylation reactions using methyl iodide or methyl-9-BBN was also possible. The facile diversification of a steroid derivative using these reactions demonstrated the synthetic utility of such complementary cross coupling reactions.

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Iron-catalysed enantioconvergent Suzuki–Miyaura cross-coupling to afford enantioenriched 1,1-diarylalkanes

Abstract: The first stereoconvergent Suzuki-Miyaura cross-coupling reaction was developed to afford enantioenriched 1,1-diarylalkanes. An iron-based complex containing a chiral cyanobis(oxazoline) ligand framework was best to obtain enantioenriched 1,1-diarylalkanes from cross-coupling reactions...

Cited by 37 publications

References 40 publications

Iron-catalyzed domino coupling reactions of π-systems

Iron-catalyzed domino coupling reactions of π-systems

Enantioselective Cross‐couplings between Halide Derivatives and Organometallics by Using Iron and Cobalt Catalysts: Formation of C−C Bonds

A Broadly Applicable Alkyl-Alkyl Suzuki-Miyaura Cross-Coupling Reaction Catalyzed by an Iron-Based Complex

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