Carbon–Carbon Bond Formation of Trifluoroacetyl Amides with Grignard Reagents via C(O)–CF3 Bond Cleavage

2019 ◽  
Vol 84 (9) ◽  
pp. 5635-5644 ◽  
Author(s):  
Longzhi Zhu ◽  
Liyuan Le ◽  
Mingpan Yan ◽  
Chak-Tong Au ◽  
Renhua Qiu ◽  
...  
Keyword(s):  
Bond Cleavage ◽  
Bond Formation ◽  
Grignard Reagents ◽  
Carbon Bond ◽  
Carbon Carbon Bond

Titanacyclopropanes as versatile intermediates for carbon-carbon bond formation in reactions with unsaturated compounds

2000 ◽  
Vol 72 (9) ◽  
pp. 1715-1719 ◽  
Author(s):  
O. G. Kulinkovich
Keyword(s):  
Reaction Mechanism ◽  
Bond Formation ◽  
Grignard Reagents ◽  
Allylic Alcohols ◽  
Ethylmagnesium Bromide ◽  
Carbon Bond ◽  
Unsaturated Compounds ◽  
Carbon Carbon Bond ◽  
Reaction Proceeds

Dialkoxytitanacyclopropane intermediates [or titanium (II)-olefin complexes] generated in situ from ethylmagnesium bromide and titanium (IV) isopropoxide react with allylic alcohols and allylic ethers to afford SN2' allylic ethylation products. The reaction proceeds with high regioselectivity and with low to high trans-/cis-stereoselectivity. This observation and others suggest a reaction mechanism involving an EtMgBr-initiated formation of titanacyclopentane ate complex 10 from titanacyclopropane-olefin complex 7 as a key step. Based on this assumption, a modified mechanism of titanium-mediated cyclopropanation of esters with Grignard reagents is proposed.

scholarly journals Beckmann Fragmentation and Successive Carbon–Carbon Bond Formation Using Grignard Reagents via Phosphonium Salt Intermediates

2016 ◽  
Vol 64 (7) ◽  
pp. 718-722 ◽  
Author(s):  
Hiromichi Fujioka ◽  
Nao Matsumoto ◽  
Yuichi Kuboki ◽  
Hidenobu Mitsukane ◽  
Reiya Ohta ◽  
...  
Keyword(s):  
Phosphonium Salt ◽  
Bond Formation ◽  
Grignard Reagents ◽  
Carbon Bond ◽  
Carbon Carbon Bond

Ring-opening of cyclic ethers with carbon–carbon bond formation by Grignard reagents

Tetrahedron ◽  
2014 ◽  
Vol 70 (33) ◽  
pp. 4942-4946 ◽  
Author(s):  
Stig Holden Christensen ◽  
Torkil Holm ◽  
Robert Madsen
Keyword(s):  
Ring Opening ◽  
Bond Formation ◽  
Grignard Reagents ◽  
Cyclic Ethers ◽  
Carbon Bond ◽  
Carbon Carbon Bond
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