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Alkenylations

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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 synergistic combination of copper and chiral amine catalysis enables an enantioselective α-vinylation of aldehydes using vinyl iodonium triflate salts. These mild catalysis provides enolizable α-formyl vinylic stereocenters without racemization or olefin transposition. These high-value coupling adducts are readily converted into various useful olefin synthons.
E. Skucas, D. W. C. MacMillan, J. Am. Chem. Soc., 2012, 134, 9090-9093.


A synergistic combination of copper and chiral amine catalysis enables an enantioselective α-alkenylation of aldehydes using boronic acids. The merger of two highly utilized and robust catalytic systems has allowed for the development of a mild and operationally trivial protocol for the direct formation of α-formyl olefins employing common building blocks for organic synthesis.
J. M Stevens. D. W. C. MacMillan, J. Am. Chem. Soc., 2013, 135, 11756-11757.


The use of gem-bis(boronates) as precursors enables a construction of quaternary α-aryl aldehydes, in which both groups are installed simultaneously. This methodology provides a general strategy to produce quaternary α-aryl aldehydes with broad scopes and synthetic convenience. In addition, gem-bis(boronates) are readily available from ketones.
P. Zheng, Y. Zhai, X. Zhao, T. Xu, Org. Lett., 2019, 21, 393-396.


Intermolecular coupling of aromatic and aliphatic ketone lithium enolates with a variety of alkenyl halides is achieved in good yields in the presence of Ni(cod)2 catalyst, an N-heterocyclic carbene (NHC) ligand, and LiI.
M. Grigalunas, T. Ankner, P.-O. Norrby, O. Wiest, P. Helquist, J. Am. Chem. Soc., 2015, 137, 7019-7022.


In a protocol for a mild, catalytic, intermolecular alkenylation of ketone enolates, Pd/Q-Phos as catalyst enables an efficient intermolecular coupling of various ketones with alkenyl bromides with a slight excess of LiHMDS at 0C.
M. Grigalunas, T. Ankner, P.-O. Norrby, O. Wiest, P. Helquist, Org. Lett., 2014, 16, 3970-3973.


KOtBu/DMSO promoted α-vinylation of aliphatic, cycloaliphatic, and alkyl aromatic (heteroaromatic) ketones with diverse arylacetylenes enables the synthesis of various β,γ-unsaturated ketones of E configuration in very good yields.
B. A. Trofimov, E. Y. Schmidt, N. V. Zorina, E. V. Ivanova, I. A. Ushakov, J. Org. Chem., 2012, 77, 6880-6886.


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 convenient and general atom transfer radical addition (ATRA) of simple nitriles, ketones, and esters to alkynes provides a wide range of β,γ-unsaturated nitriles, ketones, and esters.
Y. Xiao, Z.-Q. Liu, Org. Lett., 2019, 21, 8810-8813.


An operationally simple and scalable Cu-catalyzed asymmetric conjugate addition of trialkenylboroxines to enone diesters proceeded at room temperature. Mechanistic studies revealed that two different catalytic species work synergistically in the reaction.
K. Yasumoto, N. Kunitomo, T. Kano, Org. Lett., 2023, 25, 1497-1502.

Related


Multifunctional palladium catalysis allows a one-pot stereocontrolled synthesis of tetrasubstituted methyl ketones and enynes. The homogeneous palladium dihalide catalyst is used for the bromo-/chloroallylation of alkynes and in situ for subsequent Wacker-Tsuji oxidation or Sonogashira cross-coupling.
A. N. Thadani, V. H. Rawal, Org. Lett., 2002, 4, 4321-4323.