1016-77-9Relevant articles and documents
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Nishida,S.
, p. 2692 - 2695 (1967)
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Palladium-phosphinous acid-catalyzed cross-coupling of aliphatic and aromatic acyl chlorides with boronic acids
Ekoue-Kovi, Kekeli,Xu, Hanhui,Wolf, Christian
, p. 5773 - 5776 (2008)
The cross-coupling of aromatic and aliphatic acyl chlorides with arylboronic acids in the presence of 2.5 mol % of (t-Bu2POH)2PdCl2 (POPd) provides rapid access to ketones that are obtained in up to 93% yield. This palladium-phosphinous acid-catalyzed reaction is completed within 10 min when microwave irradiation is used, and it overcomes typical drawbacks of Friedel-Crafts acylation procedures such as harsh reaction conditions, untunable regiocontrol, and low substrate scope.
Microwave-assisted cross-coupling reaction of sodium tetraphenylborate with aroyl chlorides on palladium-doped KF/Al2O3
Wang, Jin-Xian,Yang, Yihua,Wei, Bangguo,Hu, Yulai,Fu, Ying
, p. 1381 - 1382 (2002)
A palladium-catalysed cross-coupling reaction of sodium tetraphenylborate with aroyl chloride using KF/Al2O3 as supported reagents in the presence of acetone under microwave-irradiation conditions gives unsymmetrical ketones in good high yield.
Synthesis of Farnesol Analogues through Cu(I)-Mediated Displacements of Allylic THP Ethers by Grignard Reagents
Mechelke, Mark F.,Wiemer, David F.
, p. 4821 - 4829 (1999)
The synthesis of a family of farnesol analogues, incorporating aromatic rings, has been achieved in high yields through the development of a regioselective coupling of allylic tetrahydropyranyl ethers with organometallic reagents. The allylic THP group is displaced readily by Grignard reagents in the presence of Cu(I) halides but is stable in the absence of added copper. Thus, an allylic THP group can fulfill its traditional role as a protecting group or serve as a leaving group depending on reaction conditions. An improved synthesis of (2E,6E)-10,11-dihydrofarnesol also has been accomplished using this methodology, and some preliminary studies on the reactivity and regioselectivity of THP ether displacements were conducted. The farnesol analogues reported herein may be useful probes of the importance of nonbonding interactions in enzymatic recognition of the farnesyl chain and allow development of more potent competitive inhibitors of enzymes such as farnesyl protein transferase.
Synthesis of biaryl ketones by arylation of Weinreb amides with functionalized Grignard reagents under thermodynamic controlvs.kinetic control ofN,N-Boc2-amides
Li, Guangchen,Szostak, Michal
supporting information, p. 3827 - 3831 (2020/06/03)
A highly efficient method for chemoselective synthesis of biaryl ketones by arylation of Weinreb amides (N-methoxy-N-methylamides) with functionalized Grignard reagents is reported. This protocol offers rapid entry to functionalized biaryl ketones after Mg/halide exchange with i-PrMgCl·LiCl under operationally-simple and practical reaction conditions. The scope of the method is highlighted in >40 examples, including bioactive compounds and pharmaceutical derivatives. Collectively, this transition-metal-free approach offers a major advantage over the recently established cross-coupling of amides by oxidative addition of N-C(O) bonds. Considering the utility of amide acylation reactions in modern synthesis, we expect that this method will be of broad interest.
Chemoselective Synthesis of Aryl Ketones from Amides and Grignard Reagents via C(O)-N Bond Cleavage under Catalyst-Free Conditions
Sureshbabu, Popuri,Azeez, Sadaf,Muniyappan, Nalluchamy,Sabiah, Shahulhameed,Kandasamy, Jeyakumar
, p. 11823 - 11838 (2019/10/02)
Conversion of a wide range of N-Boc amides to aryl ketones was achieved with Grignard reagents via chemoselective C(O)-N bond cleavage. The reactions proceeded under catalyst-free conditions with different aryl, alkyl, and alkynyl Grignard reagents. α-Ketoamide was successfully converted to aryl diketones, while α,β-unsaturated amide underwent 1,4-addition followed by C(O)-N bond cleavage to provide diaryl propiophenones. N-Boc amides displayed higher reactivity than Weinreb amides with Grignard reagents. A broad substrate scope, excellent yields, and quick conversion are important features of this methodology.
