Tandem catalysis: a taxonomy and illustrative review

Fogg, Deryn E.; Santos, Eduardo N. dos

doi:10.1016/j.ccr.2004.05.012

Cited by 958 publications

(512 citation statements)

References 96 publications

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“…8 At the outset of our investigations, however, it was unclear whether CO 2 could participate in cascade reductive coupling reactions via multiple bond-forming reactions. 9 Although we anticipated that reductive cascade processes based on the employment of unactivated alkyl halides, 10 probably the most challenging substrates in the cross-coupling arena, would be rather problematic, we were attracted to the challenge. 11 Specifically, such a route would offer the unique opportunity to control parasitic β-hydride elimination pathways 10 while resulting in carboxylated carbocyclic skeletons from simple precursors via distal catalytic CO 2 fixation.…”

Section: Distal Bond-formation Via Cascade Events (Unknown) = Alkyl Ementioning

confidence: 99%

Ni-Catalyzed Divergent Cyclization/Carboxylation of Unactivated Primary and Secondary Alkyl Halides with CO₂

2015

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A user-friendly Ni-catalyzed reductive cyclization/carboxylation of unactivated alkyl halides with CO 2 is described. The protocol operates under mild conditions with excellent chemoselectivity profile and a divergent syn/anti-selectivity pattern that can be easily modulated by the substrate utilized.Catalytic reductive coupling reactions of organic halides have evolved from mere curiosities to robust tools that rapidly build up molecular complexity from simple precursors.1 At present, this field of expertise remains essentially confined to bond-formation events at the initial site (Scheme 1, path a). Intriguingly, the ability to promote cascade reactions of unactivated alkyl electrophiles via multiple C-C bond-formations has virtually been unexplored (path b).2,3 If successful, such protocols would offer a unique opportunity to increase our chemical portfolio for rapidly preparing carbocyclic skeletons while dealing with bond-formation events at distal sites.

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Section: Distal Bond-formation Via Cascade Events (Unknown) = Alkyl Ementioning

confidence: 99%

Ni-Catalyzed Divergent Cyclization/Carboxylation of Unactivated Primary and Secondary Alkyl Halides with CO₂

2015

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“…This example also highlights the new and rapidly growing area of 'synergistic' domino reactions, which employ different catalysts that are tolerant of each other and possess orthogonal reactivities. [88] Cycloaddition reactions can also act as effective triggers for domino sequences. Recent examples include Nicolaou et al's synthesis of antibiotic BE-43472B, involving a stereoselective Diels-Alder/hemiacetalisation sequence [89] and Aubé and Zeng's Diels-Alder/Schmidt domino reaction in the synthesis of stenine.…”

Section: Two-component Domino Reactionsmentioning

confidence: 99%

Multi-Bond Forming Processes in Efficient Synthesis

Green¹,

Sherburn²

2013

Aust. J. Chem.

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An increasing number of synthetic organic chemists are embracing the philosophy of efficiency. Herein we highlight multi-bond forming processes, which form two or more new covalent bonds in a single synthetic operation. Such processes, which have the ability to rapidly increase structural complexity, are preeminent in contemporary synthetic organic chemistry. In this short review we classify, analyse, and contrast contemporary multi-bond forming processes, frame these cutting edge contributions within a historical context, and speculate on likely future developments in the area.

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“…[15] Such sequential reactions have been demonstrated for olefin metathesis, [16] but have hardly been developed for enyne metathesis. So far, only a one-pot combination of enyne metathesis with a Diels-Alder reaction [14,17] or a cyclopropanation [18] have been reported.…”

Section: Introductionmentioning

confidence: 99%

Enyne Metathesis–Oxidation Sequence for the Synthesis of 2‐Phosphono Pyrroles: Proof of the “Yne‐then‐Ene” Pathway

Dieltiens

Moonen

Stevens

2006

Chemistry A European J

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A new tandem reaction sequence has been developed for the synthesis of 2‐phosphono pyrroles. The sequence consists of ring‐closing enyne metathesis of a substituted aminophosphonate, containing a terminal alkyne and an internal alkene, in combination with in situ oxidation of the produced 3‐pyrrolines using tetrachloroquinone. By analyzing the formation of the end and certain byproducts, taking into account the difference in reactivity of different substrates and carefully studying spectroscopic data, it was found that the reaction proceeds by means of the “yne‐then‐ene” pathway. During the initiation phase, a new ruthenium carbene is formed which continues the propagation cycle.

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Tandem catalysis: a taxonomy and illustrative review

Cited by 958 publications

References 96 publications

Ni-Catalyzed Divergent Cyclization/Carboxylation of Unactivated Primary and Secondary Alkyl Halides with CO₂

Ni-Catalyzed Divergent Cyclization/Carboxylation of Unactivated Primary and Secondary Alkyl Halides with CO₂

Multi-Bond Forming Processes in Efficient Synthesis

Enyne Metathesis–Oxidation Sequence for the Synthesis of 2‐Phosphono Pyrroles: Proof of the “Yne‐then‐Ene” Pathway

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Tandem catalysis: a taxonomy and illustrative review

Cited by 958 publications

References 96 publications

Ni-Catalyzed Divergent Cyclization/Carboxylation of Unactivated Primary and Secondary Alkyl Halides with CO2

Ni-Catalyzed Divergent Cyclization/Carboxylation of Unactivated Primary and Secondary Alkyl Halides with CO2

Multi-Bond Forming Processes in Efficient Synthesis

Enyne Metathesis–Oxidation Sequence for the Synthesis of 2‐Phosphono Pyrroles: Proof of the “Yne‐then‐Ene” Pathway

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Product

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About

Ni-Catalyzed Divergent Cyclization/Carboxylation of Unactivated Primary and Secondary Alkyl Halides with CO₂

Ni-Catalyzed Divergent Cyclization/Carboxylation of Unactivated Primary and Secondary Alkyl Halides with CO₂