Efficient Synthesis of Functionalized Organozinc Compounds by the Direct Insertion of Zinc into Organic Iodides and Bromides

Krasovskiy, Arkady; Malakhov, Vladimir; Gavryushin, Andrei; Knöchel, Paul

doi:10.1002/anie.200601450

Cited by 426 publications

(295 citation statements)

References 24 publications

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“…(B) Knochel has outlined the preparation of organozinc reagents via direct insertion of zinc into the carbon-halogen bond in the presence of LiCl in THF at ambient temperature 18 and the subsequent reactions of these organozinc intermediates. These reagents react readily with acid chlorides, allyl halides, and tetramethylthiuram disulfide.…”

Section: Abstractsmentioning

confidence: 99%

Activated Zinc Dust

Smith¹

2009

Synlett

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This feature focuses on a reagent chosen by a postgraduate, highlighting the uses and preparation of the reagent in current research Activated Zinc DustCompiled by Craig R. Smith Craig R. Smith received his B.S. in Chemistry (2003) and M.S. in Chemistry (2005) from Youngstown State University under the direction of Professor Peter Norris. The same year, he began his Ph.D. studies at The Ohio State University under the supervision of Professor T. V. RajanBabu. Craig has recently received an ACS Organic Division Fellowship (2009). His current interests are the development of new asymmetric transformations and the synthesis of biologically active natural products.

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Section: Abstractsmentioning

confidence: 99%

Activated Zinc Dust

Smith¹

2009

Synlett

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“…The observed predominant renal-urinary clearance route is also consistent with published results. 16,17 These preliminary in vivo PET imaging results suggest that the 4-fluoro-3-iodobenzamide moiety do not appear to interfere with the biological activity of both tested peptides.…”

Section: I]/[mentioning

confidence: 69%

“…13 Precursor 4 was synthesized from TFIB by treating (perfluoro)tin bromide with an organozinc intermediate 14 generated in situ using a cobalt-Xantphoscatalyzed LiCl-mediated protocol. 15,16 Precursor 4 was thus prepared in a one-pot two-step procedure starting from TFIB, with 28% overall yield.…”

Section: I]/[mentioning

confidence: 99%

Development and Preliminary Evaluation of TFIB, a New Bimodal Prosthetic Group for Bioactive Molecule Labeling

Billaud

Vidal

Vincenot

et al. 2014

ACS Med. Chem. Lett.

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ABSTRACT:The new readily available prosthetic group, tetrafluorophenyl 4-fluoro-3-iodobenzoate (TFIB), designed for both molecular imaging and targeted radionuclide therapy purposes was radiolabeled either with fluorine or iodine radionuclides with excellent radiochemical yields and purities. These radiolabeled tags were conjugated to N,N-diethylethylenediamine to give melanin-targeting radiotracers [

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“…459 This direct insertion of zinc into organic iodides and bromides has been performed very recently adding lithium chloride, a methodology similar to the acceleration of the bromo-magnesium exchange observed after addition of this salt (see Section 3.1.1). 460 An example of the application of this methodology is the transformation of 2,5-diiodothiophene (255) into the thienylzinc-lithium chloride species 256 (after addition of 1.4 equivalents of zinc metal and lithium chloride) which afforded to ketone 257 after copper(I)-catalyzed acylation with benzoyl chloride (Scheme 76). Moreover, functionalized iodinated systems such as an acetylated 2-iodothiophene can be converted into diaryl zinc compounds after an iodo-zinc exchange using diisopropylzinc in the presence of a catalytic amount of nickel acetylacetonate to accelerate the otherwise slow halogen-zinc exchange.…”

Section: Scheme 75mentioning

confidence: 99%