Palladium-Catalyzed Synthesis of Isocoumarins and Phthalides via <i>tert</i>-Butyl Isocyanide Insertion

Fei, Xiang‐Dong; Ge, Zhi‐Yuan; Tang, Ting; Zhu, Yong‐Ming; Ji, Shun‐Jun

doi:10.1021/jo302004u

Cited by 106 publications

(40 citation statements)

References 41 publications

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“…The organic segment is connected to the isocyanide group via the nitrogen atom, not via the carbon. They are used as privileged synthons for the synthesis of other organic compounds in particular various heterocycles [23][24][25][26][27][28][29][30][31][32][33][34][35][36][37] , frequently via multicomponent reactions (MCRs) namely isocyanide multicomponent reactions (IMCRs) 25,[38][39][40][41][42][43][44][45][46][47][48][49] . Noticeably isocyanides are susceptible to polymerization 50 .…”

Section: Introductionmentioning

confidence: 99%

Isocyanide-based multicomponent reactions in the synthesis of heterocycles

2016

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Section: Introductionmentioning

confidence: 99%

Isocyanide-based multicomponent reactions in the synthesis of heterocycles

2016

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“…(77)]. [112] Aromatic ketones ( 341 , R 3 =Ar) work particularly well with minimal dependence on the electronic nature of the aromatic ring. NiCl 2 (2.5%), DPPE, and K 2 CO 3 catalyze the same condensation of tert -butyl isonitrile with ketones 341 to afford iminolactones (52–91%) with the advantage of employing a less expensive metal.…”

Section: Condensations Affording Iminesmentioning

confidence: 99%

“…Palladium acetate with DPEPhos [112] and NiCl 2 , DPPE [113] both catalyze the condensation of the regioisomeric bromo ketones 343 with tert -butyl isonitrile to afford iminophthalides that were hydrolyzed to the corresponding phthalides 344 [Eq. (78)].…”

Section: Condensations Affording Iminesmentioning

confidence: 99%

Catalytic Isonitrile Insertions and Condensations Initiated by RNC–X Complexation

et al. 2014

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Isonitriles are delicately poised chemical entities capable of being coaxed to react as nucleophiles or electrophiles. Directing this tunable reactivity with metal and non-metal catalysts provides rapid access to a large array of complex nitrogenous structures ideally functionalized for medicinal applications. Isonitrile insertion into transition metal complexes has featured in numerous synthetic and mechanistic studies, leading to rapid deployment of isonitriles in numerous catalytic processes, including multicomponent reactions (MCR). Covering the literature from 1990–2014, the present review collates reaction types to highlight reactivity trends and allow catalyst comparison.

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“…4 We have also developed a diversity-oriented synthesis of isoquinolines -one via the ligand-free Pdcatalyzed domino reaction with insertion of isocyanides into amide. 5 Inspired by the above literature and our previous report, we envisaged that the insertion of isocyanides into amide to the synthesis of substituted isoindolinone derivatives might be possible (Scheme 1).…”

Section: T-bumentioning

confidence: 99%

A Simple and Efficient Microwave-Assisted Synthesis of Substituted Isoindolinone Derivatives via Ligand-Free Pd-Catalyzed Domino C-C/C-N Coupling Reaction

Tyagi

Khan

Chauhan

2013

Synlett

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We have reported a microwave-assisted, ligand-free Pdcatalyzed domino C-C/C-N coupling reaction to construct diverse isoindolinone derivatives using amides and isocyanides as coupling partners. This strategy provides isoindolinone derivatives in moderate to good yield and high stereoselectivity. A broad range of amides has been tolerated and there is no need for extra-dry conditions in this reaction protocol, which offered highly diverse products and easy handling of the reaction.In the last decades, the transition-metal-catalyzed domino reactions with C-C or C-heteroatom bond formation have significant impact on synthetic organic chemistry. 1 Furthermore, the synthetic potential of transition-metal-catalyzed domino reactions has been significantly explored by the development of insertion reactions, in which an alkyne or alkene and carbon monoxide is inserted between the two coupling partners due to the capability of transitionmetal complex to react with the π-system. 2On the other hand, isocyanides, which are isoelectronic with carbon monoxide, have been used as synthetic surrogates of carbon monoxide in transition-metal-catalyzed domino reactions due to the potential of transition-metal complex to react with the π-system of isocyanides. In this context, a broad range of heterocycles has been synthesized using isocyanides instead of carbon monoxide in transition-metal-catalyzed domino reactions. 3 Scheme 1 Recent approaches using isocyanides as a coupling partnerR 2 R 3 O R 1 Br t-BuNC, Pd(OAc) 2 K 2 CO 3 , DPEPhos DMF, 120 °C R 1 O R 2 R 3 N t-Bu HCl, THF reflux R 1 O R 2 R 3 O Br O R 2 R 1 t-BuNC, Pd(OAc) 2 K 2 CO 3 , DPEPhos DMF, 120 °C O N R 1 HCl, THF reflux O O R 1 R 2 NH 2 R 3 NC + Br CHO Ugi-MCR R 1 N R 2 O H N O R 3 Br Pd(OAc) 2 , DMF t-BuNC, Cs 2 CO 3 MW, 150 °C, 20 min NH N R 2 R 1 O H N O R 3 (a) Ji et al. (b) our previous report (c) N H O R 1 X X = Br, I + R 2 NC Pd catalyst N O R 1 N R 2 this approach R 2 R 2 t-Bu R 1 COOHSYNLETT 2013, 24, 0645-0651 Advanced online publication: 25.02.20130 9 3 6 -5 2 1 4 1 4 3 7 -2 0 9 6

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Palladium-Catalyzed Synthesis of Isocoumarins and Phthalides via tert-Butyl Isocyanide Insertion

Cited by 106 publications

References 41 publications

Isocyanide-based multicomponent reactions in the synthesis of heterocycles

Isocyanide-based multicomponent reactions in the synthesis of heterocycles

Catalytic Isonitrile Insertions and Condensations Initiated by RNC–X Complexation

A Simple and Efficient Microwave-Assisted Synthesis of Substituted Isoindolinone Derivatives via Ligand-Free Pd-Catalyzed Domino C-C/C-N Coupling Reaction

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