Palladium-Catalyzed C-C Triple Bond Cleavage: Efficient Synthesis of 4H-Benzo[d][1,3]oxazin-4-ones

被引:86
作者
Liu, Qilun [1 ]
Chen, Pinhong [1 ,2 ]
Liu, Guosheng [1 ]
机构
[1] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China
[2] Jiangxi Normal Univ, Key Lab Funct Small Organ Mol, Minist Educ, Nanchang 330022, Peoples R China
基金
美国国家科学基金会;
关键词
Pd catalyst; azidoalkyne; aminocyclization; C-C triple bond cleavage; oxidation; LIPASE INHIBITOR; AMINOFLUORINATION; COMPLEXES; ALKYNE; TRANSFORMATION; CETILISTAT; ACCESS;
D O I
10.1021/cs300733s
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
Described herein is a new transformation of azidoalkynes by using a palladium catalyst, which involves a tandem process of aminopalladation of the alkyne and oxidative rearrangement. The reaction affords a variety of 4H-benzo[d][1,3]oxazin-4-ones. Mechanism studies support a Pd-catalyzed aminopalladation/oxidation/Baeyer-Villiger fragmentary sequence.
引用
收藏
页码:178 / 181
页数:4
相关论文
共 37 条
[1]   Nucleophilic ring-opening reaction of benzoxazinones-access to o-amino-2,2,2-trifluoroacetophenones [J].
Allendoerfer, Nadine ;
Es-Sayed, Mazen ;
Nieger, Martin ;
Braese, Stefan .
TETRAHEDRON LETTERS, 2012, 53 (04) :388-391
[2]  
Bunz UHF, 1999, ANGEW CHEM INT EDIT, V38, P478, DOI 10.1002/(SICI)1521-3773(19990215)38:4<478::AID-ANIE478>3.0.CO
[3]  
2-K
[4]   Reaction of [W(eta(2)-PhC(2)Ph)(3)(NCMe)] with o-diphenylphosphino-styrene and -allylbenzene; Evidence for novel carbon-carbon double and triple bond cleavage and alkyne insertion reactions [J].
Cairns, GA ;
Carr, N ;
Green, M ;
Mahon, MF .
CHEMICAL COMMUNICATIONS, 1996, (21) :2431-2432
[5]   Tandem Catalytic Triple-Bond Cleavage of Alkyne in Association with Aldehyde, Alkene, and Water [J].
Cha, Kyung-Mi ;
Jo, Eun-Ae ;
Jun, Chul-Ho .
SYNLETT, 2009, (18) :2939-2942
[6]   New water-soluble alkyl-carbonyl iridium complexes containing both Cp* (C5Me5-) and PAr3 (P(m-C6H4SO3Na)3):: Cleavage of C≡C and C=C bonds with water [J].
Chin, CS ;
Chong, D ;
Maeng, B ;
Ryu, J ;
Kim, H ;
Kim, M ;
Lee, H .
ORGANOMETALLICS, 2002, 21 (08) :1739-1742
[7]   THE ORGANOMETALLIC CHEMISTRY OF ALKANES [J].
CRABTREE, RH .
CHEMICAL REVIEWS, 1985, 85 (04) :245-269
[8]   Gold-catalyzed oxidative cleavage of aryl-substituted alkynyl ethers using molecular oxygen. Simultaneous degradation of C-H and single and triple carbon-carbon bonds under ambient conditions [J].
Das, Arindam ;
Chaudhuri, Rupsha ;
Liu, Rai-Shung .
CHEMICAL COMMUNICATIONS, 2009, (27) :4046-4048
[9]   A new ruthenium-catalyzed cleavage of a carbon-carbon triple bond: Efficient transformation of ethynyl alcohol into alkene and carbon monoxide [J].
Datta, S ;
Chang, CL ;
Yeh, KL ;
Liu, RS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (31) :9294-9295
[10]   Synthesis and evaluation of condensed and noncondensed heterocyclic compounds of industrial application [J].
Eissa, A. M. F. ;
El-Sayed, R. .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 2006, 43 (05) :1161-1168