58824-47-8Relevant articles and documents
Palladium-Catalyzed Synthesis of α-Methyl Ketones from Allylic Alcohols and Methanol
Biswal, Priyabrata,Samser, Shaikh,Meher, Sushanta Kumar,Chandrasekhar, Vadapalli,Venkatasubbaiah, Krishnan
supporting information, p. 413 - 419 (2021/11/01)
One-pot synthesis of α-methyl ketones starting from 1,3-diaryl propenols or 1-aryl propenols and methanol as a C1 source is demonstrated. This one-pot isomerization-methylation is catalyzed by commercially available Pd(OAc)2 with H2O as the only by-product. Mechanistic studies and deuterium labelling experiments indicate the involvement of isomerization of allyl alcohol followed by methylation through a hydrogen-borrowing pathway in these isomerization-methylation reactions.
In Situ Ring-Closing Strategy for Direct Synthesis of N-Heterocyclic Carbene Nickel Complexes and Their Application in Coupling of Allylic Alcohols with Aryl Boronic Acids
Wang, Yu-Bin,Liu, Bin-Yuan,Bu, Qingqing,Dai, Bin,Liu, Ning
supporting information, p. 2930 - 2940 (2020/06/17)
A in situ ring-closing strategy was developed for the synthesis of N-heterocyclic carbene nickel complexes. The process was carried out in air, and did not require solvent purification. The resulting nickel complexes were investigated as catalysts for the coupling of allylic alcohols with aryl boronic acids. A wide range of allylic substrates and aryl acids proved to be applicable to this catalytic system. Control experiments suggest that the Ni(0) may be the true active species in the coupling reactions. (Figure presented.).
Palladium-catalyzed regioselective synthesis of B(4,5)-or B(4)-substituted: O-carboranes containing α,β-unsaturated carbonyls
Li, Jiaoyi,Lu, Jian,Tian, Song,Wang, Qian,Zhang, Chuyi,Zhang, Jianwei,Zhou, Ling
supporting information, p. 4723 - 4727 (2020/07/13)
With the help of a carboxylic acid directing group, Pd-catalyzed regioselective synthesis of B(4,5)-or B(4)-substituted o-carboranes containing α,β-unsaturated carbonyls has been reported. The-COOH, removed during the course of the reaction, is responsible for controlling the regioselectivity. The desired products could be obtained in moderate to good yields.
Highly Enantioselective Iridium-Catalyzed Coupling Reaction of Vinyl Azides and Racemic Allylic Carbonates
Han, Min,Yang, Min,Wu, Rui,Li, Yang,Jia, Tao,Gao, Yuanji,Ni, Hai-Liang,Hu, Ping,Wang, Bi-Qin,Cao, Peng
supporting information, p. 13398 - 13405 (2020/09/02)
The iridium-catalyzed enantioselective coupling reaction of vinyl azides and allylic electrophiles is presented and provides access to β-chiral carbonyl derivatives. Vinyl azides are used as acetamide enolate or acetonitrile carbanion surrogates, leading to γ,δ-unsaturated β-substituted amides as well as nitriles with excellent enantiomeric excess. These products are readily transformed into chiral N-containing building blocks and pharmaceuticals. A mechanism is proposed to rationalize the chemoselectivity of this coupling reaction.
One-Pot Conversion of Allylic Alcohols to α-Methyl Ketones via Iron-Catalyzed Isomerization-Methylation
Latham, Daniel E.,Polidano, Kurt,Williams, Jonathan M. J.,Morrill, Louis C.
supporting information, p. 7914 - 7918 (2019/10/16)
A one-pot iron-catalyzed conversion of allylic alcohols to α-methyl ketones has been developed. This isomerization-methylation strategy utilized a (cyclopentadienone)iron(0) carbonyl complex as precatalyst and methanol as the C1 source. A diverse range of allylic alcohols undergoes isomerization-methylation to form α-methyl ketones in good isolated yields (up to 84% isolated yield).
A Convenient Palladium-Catalyzed Carbonylative Synthesis of (E)-3-Benzylidenechroman-4-ones
Wang, Wei-Feng,Peng, Jin-Bao,Qi, Xinxin,Ying, Jun,Wu, Xiao-Feng
supporting information, p. 3521 - 3524 (2019/02/14)
A convenient palladium-catalyzed carbonylation reaction for the efficient synthesis of (E)-3-benzylidenechroman-4-ones has been developed. Using TFBen as a solid CO source, a range of substituted (E)-3-benzylidenechroman-4-ones were prepared in moderate to good yields with 2-iodophenols and allyl chlorides as the substrates. Additionally, substituted quinolin-4(1H)-ones can also be obtained with 2-iodoaniline as the starting material.
Olefin Oxyamination with Unfunctionalized N-Alkylanilines
Gao, Shuang,Niggemann, Meike
supporting information, p. 1549 - 1553 (2019/02/09)
N-Alkylanilines have rarely been used in oxyamination reactions, due to the normally necessary pre-functionalization of the N-atom. Also, the formation of aminium radical cations (ARCs) of anilines bearing alkyl substituents is plagued by the ARC's tendency to instantaneously convert to α-amino radicals or iminium ions. We present a readily available reagent combination that addresses both challenges, and thus allows for an oxyamination with N-alkylanilines via ARCs as the crucial reactive intermediates and excellent diastereoselectivity. (Figure presented.).
Rh-Catalyzed Regioselective Dialkylation of Cage B-H bonds in o-Carboranes: Oxidative Heck Reactions via an Enol Isomerization
Wang, Qian,Tian, Song,Zhang, Chuyi,Li, Jiangwei,Wang, Zhixuan,Du, Yongmei,Zhou, Ling,Lu, Jian
supporting information, p. 8018 - 8021 (2019/10/19)
In the presence of a carboxylic acid directing group, Rh-catalyzed regioselective directed dialkylation of B(4,5)-H bonds in o-carboranes and oxidative coupling with allylic alcohols is reported. This strategy constructs a series of 4,5-dialkylated o-carboranes in good yields with excellent regioselectivity. A possible catalytic cycle is proposed that involves a tandem sequence of Rh-catalyzed cage B-H activation, alkene insertion, selective β-H elimination, enol isomerization, and decarboxylation.
Catalytic Asymmetric Intramolecular Bromolactonization of α,β-Unsaturated Ketones
Gan, Min,He, Hailong,Jiang, Xiaojian,Liu, Shenghui,Yi, Peng
supporting information, p. 1474 - 1478 (2019/07/15)
Enantioselective bromolactonization by using an amino-urea catalyst to generate the important bromo-containing 3,4-dihydroisocoumarins is described. Excellent yields and good enantioselectivities could be achieved for various 3,4-dihydroisocoumarin compou
Enantioselective addition of selenosulfonates to α,β-unsaturated ketones
Luo, Shilong,Zhang, Nan,Wang, Zhen,Yan, Hailong
supporting information, p. 2893 - 2901 (2018/05/03)
An organo-catalyzed enantioselective addition of selenosulfonates to α,β-unsaturated ketones was developed for the first time. With a chiral squaramide as an efficient catalyst, the desired α-selenylated ketones were obtained in a good yields with high enantioselectivity up to 89% ee, and good results could be obtained on a gram scale. The products could also be efficiently transformed into useful building blocks with a propenylic stereocenter; the strategy presented in this study may find further applications in organic synthesis.
