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Search for "difunctionalization" in Full Text gives 52 result(s) in Beilstein Journal of Organic Chemistry.

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Recent advances in transition-metal-catalyzed intermolecular carbomagnesiation and carbozincation

Kei Murakami and
Hideki Yorimitsu

Beilstein J. Org. Chem. 2013, 9, 278–302, doi:10.3762/bjoc.9.34

). The versatile 1,4-migration reactions were widely applicable for the 1,2-difunctionalization of arenes. In 2012, Gosmini reported similar cobalt-catalyzed arylzincation reactions of alkynes, which provided tri- or tetrasubstituted alkenes with high stereoselectivity [117]. Their catalytic system was

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Graphical Abstract

Scheme 1: Variation of substrates for carbomagnesiation and carbozincation in this article.

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Scheme 2: Copper-catalyzed arylmagnesiation and allylmagnesiation of alkynyl sulfone.

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Scheme 3: Copper-catalyzed four-component reaction of alkynyl sulfoxide with alkylzinc reagent, diiodomethane...

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Scheme 4: Rhodium-catalyzed reaction of aryl alkynyl ketones with arylzinc reagents.

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Scheme 5: Allylmagnesiation of propargyl alcohol, which provides the anti-addition product.

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Scheme 6: Negishi’s total synthesis of (Z)-γ-bisabolene by allylmagnesiation.

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Scheme 7: Iron-catalyzed syn-carbomagnesiation of propargylic or homopropargylic alcohol.

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Scheme 8: Mechanism of iron-catalyzed carbomagnesiation.

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Scheme 9: Regio- and stereoselective manganese-catalyzed allylmagnesiation.

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Scheme 10: Vinylation and alkylation of arylacetylene-bearing hydroxy group.

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Scheme 11: Arylmagnesiation of (2-pyridyl)silyl-substituted alkynes.

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Scheme 12: Synthesis of tamoxifen from 2g.

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Scheme 13: Controlling regioselectivity of carbocupration by attaching directing groups.

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Scheme 14: Rhodium-catalyzed carbozincation of ynamides.

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Scheme 15: Synthesis of 4-pentenenitriles through carbometalation followed by aza-Claisen rearrangement.

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Scheme 16: Uncatalyzed carbomagnesiation of cyclopropenes.

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Scheme 17: Iron-catalyzed carbometalation of cyclopropenes.

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Scheme 18: Enantioselective carbozincation of cyclopropenes.

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Scheme 19: Copper-catalyzed facially selective carbomagnesiation.

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Scheme 20: Arylmagnesiation of cyclopropenes.

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Scheme 21: Enantioselective methylmagnesiation of cyclopropenes without catalyst.

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Scheme 22: Copper-catalyzed carbozincation.

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Scheme 23: Enantioselective ethylzincation of cyclopropenes.

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Scheme 24: Nickel-catalyzed ring-opening aryl- and alkenylmagnesiation of a methylenecyclopropane.

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Scheme 25: Reaction mechanism.

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Scheme 26: Nickel-catalyzed carbomagnesiation of arylacetylene and dialkylacetylene.

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Scheme 27: Nickel-catalyzed carbozincation of arylacetylenes and its application to the synthesis of tamoxifen....

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Scheme 28: Bristol-Myers Squibb’s nickel-catalyzed phenylzincation.

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Scheme 29: Iron/NHC-catalyzed arylmagnesiation of aryl(alkyl)acetylene.

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Scheme 30: Iron/copper-cocatalyzed alkylmagnesiation of aryl(alkyl)acetylenes.

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Scheme 31: Iron-catalyzed hydrometalation.

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Scheme 32: Iron/copper-cocatalyzed arylmagnesiation of dialkylacetylenes.

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Scheme 33: Chromium-catalyzed arylmagnesiation of alkynes.

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Scheme 34: Cobalt-catalyzed arylzincation of alkynes.

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Scheme 35: Cobalt-catalyzed formation of arylzinc reagents and subsequent arylzincation of alkynes.

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Scheme 36: Cobalt-catalyzed benzylzincation of dialkylacetylene and aryl(alkyl)acetylenes.

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Scheme 37: Synthesis of estrogen receptor antagonist.

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Scheme 38: Cobalt-catalyzed allylzincation of aryl-substituted alkynes.

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Scheme 39: Silver-catalyzed alkylmagnesiation of terminal alkyne.

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Scheme 40: Proposed mechanism of silver-catalyzed alkylmagnesiation.

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Scheme 41: Zirconium-catalyzed ethylzincation of terminal alkenes.

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Scheme 42: Zirconium-catalyzed alkylmagnesiation.

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Scheme 43: Titanium-catalyzed carbomagnesiation.

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Scheme 44: Three-component coupling reaction.

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Scheme 45: Iron-catalyzed arylzincation reaction of oxabicyclic alkenes.

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Scheme 46: Reaction of allenyl ketones with organomagnesium reagent.

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Scheme 47: Regio- and stereoselective reaction of a 2,3-allenoate.

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Scheme 48: Three-component coupling reaction of 1,2-allenoate, organozinc reagent, and ketone.

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Scheme 49: Proposed mechanism for a rhodium-catalyzed arylzincation of allenes.

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Scheme 50: Synthesis of skipped polyenes by iterative arylzincation/allenylation reaction.

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Scheme 51: Synthesis of 1,4-diorganomagnesium compound from 1,2-dienes.

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Scheme 52: Synthesis of tricyclic compounds.

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Scheme 53: Manganese-catalyzed allylmagnesiation of allenes.

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Scheme 54: Copper-catalyzed alkylmagnesiation of 1,3-dienes and 1,3-enynes.

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Scheme 55: Chromium-catalyzed methallylmagnesiation of 1,6-diynes.

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Scheme 56: Chromium-catalyzed allylmagnesiation of 1,6-enynes.

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Scheme 57: Proposed mechanism of the chromium-catalyzed methallylmagnesiation.

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Album

Review

Published 11 Feb 2013

Full text

Alkoxide-induced ring opening of bicyclic 2-vinylcyclobutanones: A convenient synthesis of 2-vinyl-substituted 3-cycloalkene-1-carboxylic acid esters

Xiufang Ji,
Zhiming Li,
Quanrui Wang and
Andreas Goeke

Beilstein J. Org. Chem. 2012, 8, 650–657, doi:10.3762/bjoc.8.72

[18][19][20][21][22][23]. Ring-opening reactions of cyclobutanones are expected to be a valuable methodology for vicinal difunctionalization of double bonds. A prerequisite for this reaction to take place is the presence at C-2 of substituents capable of stabilizing the developing vicinal carbanion [6

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