Categories: C-C Bond Formation > Oxygen-containing molecules > Carboxylic Acids and Derivatives
Alkenylations
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Recent Literature
2-Chloroacetates as well as secondary and tertiary 2-chloroacetamides were
successfully employed as electrophiles in the Suzuki-Miyaura cross-coupling
reaction with potassium (E)- and (Z)-alkenyltrifluoroborates,
affording the corresponding (E)- and (Z)-β,γ-unsaturated esters
and amides in high yield.
G. A. Molander, T. Barcellos, K. M. Traister, Org. Lett., 2013,
15, 3342-3345.
A catalytic asymmetric cross-coupling of α-halo carbonyl compounds with aryl
metal reagents generates synthetically useful α-aryl carboxylic acid derivatives
in good enantiomeric excess. The method can also be applied to enantioselective
alkenylation reactions.
X. Dai, N. A. Strotman, G. C. Fu, J. Am. Chem. Soc., 2008,
130, 3302-3303.
The reaction between aryl- or vinylboroxines with
α-diazocarbonyl compounds offers an alternative approach for α-arylation and α-vinylation of carbonyl
compounds. α-Arylated or α-vinylated
carbonyl compounds are formed under mild conditions.
C. Peng, W. Zhang, G. Yan, J. Wang, Org. Lett., 2009,
11, 1667-1670.
A radical alkenylation reaction of α-halo carbonyl compounds with
styrylindium dichloride as well as unactivated alkenylindiums proceeded in
the presence of triethylborane. The geometry of the carbon-carbon double
bonds was retained. Efficient one-pot strategies were developed.
K. Takami, H. Yorimitsu, K. Oshima, Org. Lett.,
2004,
6, 4555-4558.
A kinetic-controlled photocatalyst-free visible-light-induced stereoselective
synthesis of synthetically important α,α-gem-difluoro-Z-allyl esters was
succeeded at room temperature in good yields and excellent Z-selectivity
through a reductive radical ethoxycarbonyldifluoromethylation of terminal aryl
alkynes with blue LED (465 nm)-excited Hantzsch ester.
J. Hao, W. Ding, Z. Zheng, L. Sun, J. Dong, M. Li, W. Wan, J. Org. Chem., 2022, 87,
13750-13756.
Phosphazene P4-tBu effectively catalyzes a nucleophilic substitution
reaction of gem-difluoroalkenes with ketene silyl acetals under mild
conditions to provide monofluoroalkenes possessing an alkoxycarbonylmethyl group
in high yields with high Z selectivities.
A. Kondoh, K. Koda, M. Terada,
Org. Lett., 2019, 21, 2277-2280.
An effient cobalt-catalyzed enantioselective vinylation of α-ketoesters,
isatins, and imines delivers a range of synthetically useful allylic alcohols
and amines in high enantiopurity. This convenient method employs commercially
available and easy to handle catalysts and reagents.
Y. Huang, R.-Z. Huang, Y. Zhao, J. Am. Chem. Soc., 2016,
138, 6571-6576.
In a ligand-controlled cobalt-catalyzed regiodivergent alkyne hydroalkylation
of terminal alkynes with alkyl halides, use of bisoxazoline and
pyridine-oxazoline ligands provided (E)-1,2-disubstituted and
1,1-disubstituted alkenes with high E/Z stereoselectivity and
regioisomeric ratio. Internal alkynes provide trisubstituted alkenes. The
methods show excellent functional group compatibility.
Y. Li, D. Liu, L. Wan, J.-Y. Zhang, X. Lu, Y. Fu, J. Am. Chem. Soc.,
2022, 144, 13961-13972.
In a ligand-controlled cobalt-catalyzed regiodivergent alkyne hydroalkylation
of terminal alkynes with alkyl halides, use of bisoxazoline and
pyridine-oxazoline ligands provided (E)-1,2-disubstituted and
1,1-disubstituted alkenes with high E/Z stereoselectivity and
regioisomeric ratio. Internal alkynes provide trisubstituted alkenes. The
methods show excellent functional group compatibility.
Y. Li, D. Liu, L. Wan, J.-Y. Zhang, X. Lu, Y. Fu, J. Am. Chem. Soc.,
2022, 144, 13961-13972.
Related
Substituted allylic zinc reagents, prepared via direct metal insertion in
substituted allylic halides, react readily with a broad range of acid chlorides
and chloroformates to yield the corresponding α-substituted β,γ-unsaturated
ketones and esters in high yield and perfect regioselectivity.
C. Sämann, P. Knochel, Synthesis, 2013, 45,
1870-1876.