Methods of Preparation of Organometallic Compounds.

Jones, Reuben G.; Gilman, Henry

doi:10.1021/cr60171a004

Cited by 72 publications

(14 citation statements)

References 234 publications

(322 reference statements)

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“…Entries 1 and 2 proceeded directly from the commercially available organolithium reagent. For entries 3 and 4, the organolithium agents were prepared by lithium-halogen exchange using 4-bromoanisole34 and 2-bromopropene,35 respectively. Not unexpectedly, the β -lactam carbonyl is fully protected by the large trityl group.…”

Section: Synthesis and Related Studiesmentioning

confidence: 99%

Enantiomerically Pure trans-β-Lactams from α-Amino Acids via Compact Fluorescent Light (CFL) Continuous-Flow Photolysis

et al. 2010

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Photolysis of α-diazo N-methoxy-N-methyl (Weinreb) β-ketoamides derived from enantiomerically pure (EP) α-amino acids affords the corresponding EP β-lactam via an intramolecular Wolff rearrangement. Photochemistry is promoted with either standard UV irradiation or through the use of a 100W compact fluorescent light (CFL); the latter affords a safe and environmentally friendly alternative to standard photolysis conditions. A continuous-flow photochemical reactor, made from inexpensive laboratory equipment, expedites reaction times and is amenable to scale-up. Diastereoselectivity (cis or trans) of the product β-lactams has been shown to vary from modest to nearly complete. An extremely facile, atom-economical method for the epimerization of the product mixture to the trans isomer, generally highly crystalline, has been developed. Evidence is presented for C-3 epimerization of Weinreb amide structures via a non-basic, purely thermal route. Subsequent transformations of both the Weinreb amide at C-3 (β-lactam numbering) and amino acid side chain at C-4 are well tolerated, allowing for a versatile approach to diverse β-lactam structures. The technology is showcased in the synthesis of a common intermediate used toward several carbapenem-derived structures starting from unfunctionalized aspartic acid.

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Section: Synthesis and Related Studiesmentioning

confidence: 99%

Enantiomerically Pure trans-β-Lactams from α-Amino Acids via Compact Fluorescent Light (CFL) Continuous-Flow Photolysis

et al. 2010

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“…The introduction of the alkynyl group to organic molecules is an important synthetic transformation in organic synthesis [ 1 – 4 ]. Recently, cyclic iodine(III) reagents (CIR)-substituted alkynes, alkynylbenziodoxoles, were developed with readily preparation and shelf-stableness [ 5 – 10 ].…”

Section: Introductionmentioning

confidence: 99%

Investigations of alkynylbenziodoxole derivatives for radical alkynylations in photoredox catalysis

Pan

Jia

Chen

et al. 2018

Beilstein J. Org. Chem.

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The alkynylbenziodoxole derivatives are recently developed alkynylation reagents in organic synthesis, which demonstrate excellent radical alkynylation reactivity in photoredox catalysis reactions. Herein we report the synthesis of alkynylbenziodoxole derivatives with difluoro, monofluoro, monomethoxy, and dimethoxy substitution on the benziodoxole moiety, and investigated their radical alkynylation reactivity for the first time. A series of mechanistic experiments were conducted to study the radical acceptor and oxidative quencher reactivity of alkynylbenziodoxoles, in which unsubstituted alkynylbenziodoxoles played balancing roles in both processes, while electron-rich benziodoxole derivatives demonstrate synthetic advantages in some cases.

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“…Although this reaction was reported by C. S. Marvel in 1927 [40], G. Wittig [41] and H. Gilman [42–44] were the first to apply it in organic synthesis in the late thirties. Since then, this reaction has been considered as a mature method lacking both appeal and surprise [33], and only new applications of this reaction or mechanistic studies have been reported [30,32–33 45–55]. However, in the last few years, the halogen–metal permutation has recaptured its former role as one of the most important and versatile methods in organic synthesis.…”

Section: Introductionmentioning

confidence: 99%

Bromine–lithium exchange: An efficient tool in the modular construction of biaryl ligands

Bonnafoux¹,

Leroux²,

Colobert³

2011

Beilstein J. Org. Chem.

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SummaryRegioselective bromine–lithium exchange reactions on polybrominated biaryls enable the modular synthesis of various polysubstituted biphenyls such as bis(dialkylphosphino)-, bis(diarylphosphino)- and dialkyl(diaryl)phosphinobiphenyls. All permutations of substituents at the ortho positions of the biphenyls are possible. In a similar manner, one can gain access to monophosphine analogues. So far, such a process, based on the effective discrimination between bromine atoms as a function of their chemical environment, has been observed only sporadically.

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Methods of Preparation of Organometallic Compounds.

Cited by 72 publications

References 234 publications

Enantiomerically Pure trans-β-Lactams from α-Amino Acids via Compact Fluorescent Light (CFL) Continuous-Flow Photolysis

Enantiomerically Pure trans-β-Lactams from α-Amino Acids via Compact Fluorescent Light (CFL) Continuous-Flow Photolysis

Investigations of alkynylbenziodoxole derivatives for radical alkynylations in photoredox catalysis

Bromine–lithium exchange: An efficient tool in the modular construction of biaryl ligands

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