Reaction of an Alkynyl Grignard Reagent with an Alkyl Halide or Equivalent

2008 ◽  
pp. 1
Author(s):  
R. A. Aitken ◽  
K. Aitken
Keyword(s):  
Grignard Reagent ◽  
Alkyl Halide

Carbon–Carbon Bond Formation: The Bergman Synthesis of (+)-Fuligocandin B

2015 ◽  
Author(s):  
Douglass F. Taber
Keyword(s):  
Grignard Reagent ◽  
Alkyl Halide ◽  
Secondary Alcohol ◽  
Ni Catalyst ◽  
West Virginia University ◽  
Carbon Carbon Bond ◽  
Peking University ◽  
National University ◽  
The University ◽  
École Polytechnique

Xile Hu of the Ecole Polytechnique Fédérale de Lausanne optimized (J. Am. Chem. Soc. 2011, 133, 7084) a Ni catalyst for the coupling of a Grignard reagent 2 with a secondary alkyl halide 1. Duk Keun An of Kangwon National University devised (Tetrahedron Lett. 2011, 52, 1718; Chem. Commun. 2011, 47, 3281) a strategy for the reductive coupling of an ester 4 with a Grignard reagent 2 to give the secondary alcohol. Daniel J. Weix of the University of Rochester added (Org. Lett. 2011, 13, 2766) the halide 7 in a conjugate sense to the bromoenone 6, setting the stage for further organometallic coupling. James Y. Becker of the Ben-Gurion University of the Negev effected (J. Org. Chem. 2011, 76, 4710) Kolbe coupling of the silyl acid 9 to give the decarboxylated dimer 10. Shi-Kai Tian of USTC Hefei showed (Chem. Commun. 2011, 47, 2158) that depending on the sulfonyl group used, the coupling of 11 with 12 could be directed cleanly toward either the Z or the E product. Yoichiro Kuninobu and Kazuhiko Takai of Okayama University added (Org. Lett. 2011, 13, 2959) the sulfonyl ketone 14 to the alkyne 13 to form the trisubstituted alkene 15. Jianbo Wang of Peking University assembled (Angew. Chem. Int. Ed. 2011, 50, 3510) the trisubstituted alkene 18 by adding the diazo ester 16 to the alkyne 17. Gangguo Zhu of Zhejiang Normal University constructed (J. Org. Chem. 2011, 76, 4071) the versatile tetrasubstituted alkene 21 by adding the chloroalkyne 19 to acrolein 20. Other more substituted acceptors worked as well. Chunxiang Kuang of Tongji University and Qing Yang of Fudan University effected (Tetrahedron Lett. 2011, 52, 992) elimination of 22 to 23 by stirring with Cs2CO3 at 115°C in DMSO overnight. Toshiaki Murai of Gifu University created (Chem. Lett. 2011, 40, 70) a propargyl anion by condensing 24 with 25 then adding 26. Xiaodong Shi of West Virginia University found (Org. Lett. 2011, 13, 2618) that the enantiomerically enriched propargyl ether 29 could be rearranged to the trisubsituted allene 30 with retention of the ee and with high de.

Carbon–Carbon Bond Construction: The Baran Synthesis of (+)-Chromazonarol

2015 ◽  
Author(s):  
Douglass F. Taber
Keyword(s):  
Grignard Reagent ◽  
Iron Catalyst ◽  
Alkyl Halide ◽  
Titanocene Dichloride ◽  
Secondary Amide ◽  
Reductive Coupling ◽  
Quaternary Centers ◽  
Carbon Carbon Bond ◽  
The University

Daniel J. Weix of the University of Rochester effected (Org. Lett. 2012, 14, 1476) the in situ reductive coupling of an alkyl halide 2 with an acid chloride 1 to deliver the ketone 3. André B. Charette of the Université de Montréal (not illustrated) developed (Nature Chem. 2012, 4, 228) an alternative route to ketones by the coupling of an organometallic with an in situ-activated secondary amide. Mahbub Alam and Christopher Wise of the Merck, Sharpe and Dohme UK chemical process group optimized (Org. Process Res. Dev. 2012, 16, 453) the opening of an epoxide 4 with a Grignard reagent 5. Ling Song of the Fujian Institute of Research on the Structure of Matter optimized (J. Org. Chem. 2012, 77, 4645) conditions for the 1,2-addition of a Grignard reagent (not illustrated) to a readily enolizable ketone. Wei-Wei Liao of Jilin University conceived (Org. Lett. 2012, 14, 2354) of an elegant assembly of highly functionalized quaternary centers, as illustrated by the conversion of 7 to 8. Antonio Rosales of the University of Granada and Ignacio Rodríguez-García of the University of Almería prepared (J. Org. Chem. 2012, 77, 4171) free radicals by reduction of an ozonide 9 in the presence of catalytic titanocene dichloride. In the absence of the acceptor 10, the dimer of the radical was obtained, presenting a simple alternative to the classic Kolbe coupling. Marc L. Snapper of Boston College found (Eur. J. Org. Chem. 2012, 2308) that the difficult ketone 12 could be methylenated following a modified Peterson protocol. Yoshito Kishi of Harvard University optimized (Org. Lett. 2012, 14, 86) the coupling of 15 with 16 to give 17. Masaharu Nakamura of Kyoto University devised (J. Org. Chem. 2012, 77, 1168) an iron catalyst for the coupling of 18 with 19. The specific preparation of trisubsituted alkenes is an ongoing challenge. Quanri Wang of Fudan University and Andreas Goeke of Givaudan Shanghai fragmented (Angew. Chem. Int. Ed. 2012, 51, 5647) the ketone 21 by exposure to 22 to give the macrolide 23 with high stereocontrol.

C–C Bond Construction: The Galano Synthesis of 8-F3t-Isoprostane

2017 ◽  
Author(s):  
Douglass F. Taber
Keyword(s):  
Carbon Monoxide ◽  
Grignard Reagent ◽  
Alkyl Halide ◽  
Boston College ◽  
Pinacol Rearrangement ◽  
Alpha Olefin ◽  
Osaka Prefecture ◽  
The University ◽  
École Polytechnique

Nobuaki Kambe of Osaka University devised (Synthesis 2014, 46, 1583) simple con­ditions for coupling an alkyl halide 1 with a Grignard reagent 2, leading to 3. Michael J. Chetcuti and Vincent Ritleng of the Université de Strasbourg arylated (Chem. Commun. 2014, 50, 4624) the ketone 4 with 5 to give 6. Ilhyong Ryu of Osaka Prefecture University effected (J. Org. Chem. 2014, 79, 3999) net conjugate acylation of the enone 8 to give 9 by reducing 7 in the presence of carbon monoxide. Yasushi Obora of Kansai University employed (Chem. Commun. 2014, 50, 2491) a borrowed hydrogen strategy to effect the net methylation of 10 to 11. There have been many examples of the alkylation of ketones using variations on this strategy. Robert H. Grubbs and Brian M. Stoltz of Caltech decarboxylated (Adv. Synth. Catal. 2014, 356, 130) an acid 12 to the corresponding alpha olefin 13. Lindsey O. Davis of Berry College combined (Tetrahedron Lett. 2014, 55, 3100) the imine 14 with the aldehyde 15 in the presence of 16 to give the enone 17. Masahiro Miyazawa of the University of Toyoma maintained (Synlett 2014, 25, 531) the geometric purity of 18 while coupling it with Me₃Al to give the diene 19. Naoki Kanoh of Tohoku University used (Eur. J. Org. Chem. 2014, 1376) the Micalizio protocol to add 22 with 21 to 20 to give the triene 23. Xile Hu of the Ecole Polytechnique Fédérale de Lausanne coupled (Org. Lett. 2014, 16, 2566) 25 with the iodide 24 to give the alkyne 26. Keiji Tanino of Hokkaido University prepared (Tetrahedron Lett. 2014, 55, 1097) the α-quaternary alkyne 29 by 1,2-addition of 28 to the ketone 27 followed by pinacol rearrangement. Zhaoguo Zhang of Shanghai Jiao Tong University and Tahar Ayad and Virginie Ratovelomanana-Vidal of Chimie ParisTech coupled (ACS Catal. 2014, 4, 44) 31 with the dienyl bromide 30 to deliver the disubstituted allene 32 in high ee. Amir H. Hoveyda of Boston College developed (Angew. Chem. Int. Ed. 2013, 52, 7694) a procedure for the preparation of alkynes such as 33 in substantial ee.

Hydrogen-halide versus alkyl-halide oxidative addition in dimethyl platinum(II) complexes: Crystal structure of [PtBr2(bpy)]

2007 ◽  
Vol 360 (8) ◽  
pp. 2661-2668 ◽  
Author(s):  
Badri Z. Momeni ◽  
Saeideh Hamzeh ◽  
Simin S. Hosseini ◽  
Frank Rominger
Keyword(s):  
Crystal Structure ◽  
Alkyl Halide ◽  
Oxidative Addition ◽  
Hydrogen Halide

scholarly journals Low-valent dialkoxytitanium(ii): a useful tool for the synthesis of functionalized seven-membered ring compounds

2021 ◽  
Vol 57 (29) ◽  
pp. 3603-3606
Author(s):  
Florent Bodinier ◽  
Youssouf Sanogo ◽  
Janick Ardisson ◽  
Marie-Isabelle Lannou ◽  
Geoffroy Sorin
Keyword(s):  
Grignard Reagent ◽  
Membered Ring ◽  
Ring Compounds ◽  
Low Valent

Herein, we describe unprecedented access to all-carbon or heterocyclic seven-membered ring frameworks from 1,8-ene-ynes promoted by inexpensive low-valent titanium(ii) species, readily available from a combination of Ti(OiPr)4 and Grignard reagent.

Facile intramolecular cyclization of an olefinic grignard reagent

1966 ◽  
Vol 7 (36) ◽  
pp. 4297-4301 ◽  
Author(s):  
Herman G. Richey ◽  
Thomas C. Rees
Keyword(s):  
Intramolecular Cyclization ◽  
Grignard Reagent
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