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Search for "styrene derivatives" in Full Text gives 52 result(s) in Beilstein Journal of Organic Chemistry.
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
- 37). Although the cobalt-catalyzed allylzincation reactions of dialkylacetylenes resulted in low yield, the reactions of arylacetylenes provided various tri- or tetrasubstituted styrene derivatives (Scheme 38) [119][120]. Kambe reported a rare example of silver catalysis for carbomagnesiation
Graphical Abstract
Scheme 1: Variation of substrates for carbomagnesiation and carbozincation in this article.
Scheme 2: Copper-catalyzed arylmagnesiation and allylmagnesiation of alkynyl sulfone.
Scheme 3: Copper-catalyzed four-component reaction of alkynyl sulfoxide with alkylzinc reagent, diiodomethane...
Scheme 4: Rhodium-catalyzed reaction of aryl alkynyl ketones with arylzinc reagents.
Scheme 5: Allylmagnesiation of propargyl alcohol, which provides the anti-addition product.
Scheme 6: Negishi’s total synthesis of (Z)-γ-bisabolene by allylmagnesiation.
Scheme 7: Iron-catalyzed syn-carbomagnesiation of propargylic or homopropargylic alcohol.
Scheme 8: Mechanism of iron-catalyzed carbomagnesiation.
Scheme 9: Regio- and stereoselective manganese-catalyzed allylmagnesiation.
Scheme 10: Vinylation and alkylation of arylacetylene-bearing hydroxy group.
Scheme 11: Arylmagnesiation of (2-pyridyl)silyl-substituted alkynes.
Scheme 12: Synthesis of tamoxifen from 2g.
Scheme 13: Controlling regioselectivity of carbocupration by attaching directing groups.
Scheme 14: Rhodium-catalyzed carbozincation of ynamides.
Scheme 15: Synthesis of 4-pentenenitriles through carbometalation followed by aza-Claisen rearrangement.
Scheme 16: Uncatalyzed carbomagnesiation of cyclopropenes.
Scheme 17: Iron-catalyzed carbometalation of cyclopropenes.
Scheme 18: Enantioselective carbozincation of cyclopropenes.
Scheme 19: Copper-catalyzed facially selective carbomagnesiation.
Scheme 20: Arylmagnesiation of cyclopropenes.
Scheme 21: Enantioselective methylmagnesiation of cyclopropenes without catalyst.
Scheme 22: Copper-catalyzed carbozincation.
Scheme 23: Enantioselective ethylzincation of cyclopropenes.
Scheme 24: Nickel-catalyzed ring-opening aryl- and alkenylmagnesiation of a methylenecyclopropane.
Scheme 25: Reaction mechanism.
Scheme 26: Nickel-catalyzed carbomagnesiation of arylacetylene and dialkylacetylene.
Scheme 27: Nickel-catalyzed carbozincation of arylacetylenes and its application to the synthesis of tamoxifen....
Scheme 28: Bristol-Myers Squibb’s nickel-catalyzed phenylzincation.
Scheme 29: Iron/NHC-catalyzed arylmagnesiation of aryl(alkyl)acetylene.
Scheme 30: Iron/copper-cocatalyzed alkylmagnesiation of aryl(alkyl)acetylenes.
Scheme 31: Iron-catalyzed hydrometalation.
Scheme 32: Iron/copper-cocatalyzed arylmagnesiation of dialkylacetylenes.
Scheme 33: Chromium-catalyzed arylmagnesiation of alkynes.
Scheme 34: Cobalt-catalyzed arylzincation of alkynes.
Scheme 35: Cobalt-catalyzed formation of arylzinc reagents and subsequent arylzincation of alkynes.
Scheme 36: Cobalt-catalyzed benzylzincation of dialkylacetylene and aryl(alkyl)acetylenes.
Scheme 37: Synthesis of estrogen receptor antagonist.
Scheme 38: Cobalt-catalyzed allylzincation of aryl-substituted alkynes.
Scheme 39: Silver-catalyzed alkylmagnesiation of terminal alkyne.
Scheme 40: Proposed mechanism of silver-catalyzed alkylmagnesiation.
Scheme 41: Zirconium-catalyzed ethylzincation of terminal alkenes.
Scheme 42: Zirconium-catalyzed alkylmagnesiation.
Scheme 43: Titanium-catalyzed carbomagnesiation.
Scheme 44: Three-component coupling reaction.
Scheme 45: Iron-catalyzed arylzincation reaction of oxabicyclic alkenes.
Scheme 46: Reaction of allenyl ketones with organomagnesium reagent.
Scheme 47: Regio- and stereoselective reaction of a 2,3-allenoate.
Scheme 48: Three-component coupling reaction of 1,2-allenoate, organozinc reagent, and ketone.
Scheme 49: Proposed mechanism for a rhodium-catalyzed arylzincation of allenes.
Scheme 50: Synthesis of skipped polyenes by iterative arylzincation/allenylation reaction.
Scheme 51: Synthesis of 1,4-diorganomagnesium compound from 1,2-dienes.
Scheme 52: Synthesis of tricyclic compounds.
Scheme 53: Manganese-catalyzed allylmagnesiation of allenes.
Scheme 54: Copper-catalyzed alkylmagnesiation of 1,3-dienes and 1,3-enynes.
Scheme 55: Chromium-catalyzed methallylmagnesiation of 1,6-diynes.
Scheme 56: Chromium-catalyzed allylmagnesiation of 1,6-enynes.
Scheme 57: Proposed mechanism of the chromium-catalyzed methallylmagnesiation.
Highly substituted benzannulated cyclooctanol derivatives by samarium diiodide-induced cyclizations
- Jakub Saadi,
- Irene Brüdgam and
- Hans-Ulrich Reissig
Beilstein J. Org. Chem. 2010, 6, 1229–1245, doi:10.3762/bjoc.6.141
- -trig cyclizations to cycloheptanol derivatives have been observed. In examples with high steric hindrance the ketyl–aryl coupling can be a competing process. Keywords: cyclooctanes; ketones; ketyls; medium-sized rings; samarium diiodide; single electron transfer; styrene derivatives; radicals
Graphical Abstract
Scheme 1: SmI2-induced cyclizations of styryl-substituted γ-ketoesters A to benzannulated cyclooctanol deriva...
Scheme 2: Three-step synthesis of precursor 4 starting from siloxycyclopropane derivative 1.
Scheme 3: Attempted cyclizations of diastereomeric cycloheptanone derivatives 5a and 5b.
Scheme 4: Samarium diiodide-induced cyclization of γ-ketoester 7a to tricyclic compound 8.
Scheme 5: Samarium diiodide-induced cyclizations of methyl ketone 4 and iso-propyl ketone 11.
Figure 1: NOESY-correlation for compound 10.
Figure 2: NOESY-correlation for compound 9.
Scheme 6: Assumed transition structures and intermediates A, B, or C for the cyclizations of (2-propenyl)phen...
Scheme 7: Reductive fragmentation of highly hindered ketoester 14.
Scheme 8: Samarium diiodide-induced cyclization of phenyl-substituted substrate 16 leading to lactones 17a an...
Figure 3: Molecular structure (Diamond [52]) of compound 17b.
Scheme 9: Samarium diiodide-induced cyclizations of (E)-(1-propenyl)phenyl-substituted γ-ketoesters 18, 21, a...
Figure 4: Proposed transition structure for the cyclization of (E)-1-propenyl-substituted substrates (HMPA li...
Scheme 10: Attempted samarium diiodide-induced cyclizations with (E)-1-propenyl-substituted precursors 26a and ...
Scheme 11: Attempted samarium diiodide-induced cyclization of (Z)-1-propenyl-substituted precursor 30.
Scheme 12: Samarium diiodide-induced cyclizations of γ-ketoesters 33 and 36.
Scheme 13: Samarium diiodide-induced cyclizations of diastereomeric stilbenyl-substituted γ-ketoesters 38a and ...
Figure 5: Molecular structure (Diamond [52]) of compound 40.
Scheme 14: Attempted cyclization of β-dialkyl-substituted styrene derivative 41.
Scheme 15: Typical products of samarium diiodide-induced 8-endo-trig cyclizations of α-styryl-substituted γ-ke...
Scheme 16: Typical products of samarium diiodide-induced 8-endo-trig cyclizations of β-styryl-substituted γ-ke...
