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2 article(s) from Lassalas, Pierrik

Synthesis of the heterocyclic core of the D-series GE2270

Christophe Berini,
Thibaut Martin,
Pierrik Lassalas,
Francis Marsais,
Christine Baudequin and
Christophe Hoarau

Beilstein J. Org. Chem. 2017, 13, 1407–1412, doi:10.3762/bjoc.13.137

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Figure 1: Main synthetic strategies towards heterocyclic cores of D-series GE2270 and our present one.

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Scheme 1: Synthesis of trithiazolylpyridine 9. Reaction conditions: a) Pd(OAc)₂ (5 mol %), CyJohnPhos (10 mol...

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Scheme 2: Synthesis of chiral thioamide 16. Reaction conditions: a) SnCl₂∙2H₂O, dioxane/H₂O (1:3), 0 °C to rt...

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Scheme 3: Synthesis of the heterocyclic core of the D-series GE2270. Reaction conditions: a) TBDMSOTf, NEt₃, ...

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Full Research Paper

Published 17 Jul 2017

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Recent advances in direct C–H arylation: Methodology, selectivity and mechanism in oxazole series

Cécile Verrier,
Pierrik Lassalas,
Laure Théveau,
Guy Quéguiner,
François Trécourt,
Francis Marsais and
Christophe Hoarau

Beilstein J. Org. Chem. 2011, 7, 1584–1601, doi:10.3762/bjoc.7.187

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Scheme 1: Stoichiometric and catalytic direct (hetero)arylation of arenes.

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Scheme 2: Stille and Negishi cross-coupling methodologies in oxazole series [28,30,31,33,34].

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Scheme 3: Stoichiometric direct (hetero)arylation of (benz)oxazole with magnesate bases [35].

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Scheme 4: Ohta's pioneering catalytic direct C5-selective pyrazinylation of oxazole [36,37].

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Scheme 5: Preparation of pharmaceutical compounds by following the pioneering Ohta protocol [38,39].

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Scheme 6: Miura’s pioneering catalytic direct arylations of (benz)oxazoles [40]. ^aIsolated yield.

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Scheme 7: Pd(0)- and Cu(I)-catalyzed direct C2-selective arylation of (benz)oxazoles [41-44].

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Scheme 8: Cu(I)-catalyzed direct C2-selective arylations of (benz)oxazoles [40,45-47].

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Scheme 9: Copper-free Pd(0)-catalyzed direct C5- and C2-selective arylation of oxazole-4-carboxylate esters [48-50,52].

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Scheme 10: Iterative synthesis of bis- and trioxazoles [51].

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Scheme 11: Preparation of DPO- and POPOP-analogues [53].

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Scheme 12: Pd(0)-catalyzed direct arylation of benzoxazole with aryl chlorides [54].

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Scheme 13: Pd(0)-catalyzed direct C2-selective arylation of (benz)oxazoles with bromides and chlorides using b...

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Scheme 14: Palladium-catalyzed direct arylation of oxazoles under green conditions; (a) Zhuralev direct arylat...

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Scheme 15: Pd(0)-catalyzed C2- and C5-selective (hetero)arylation of oxazole [63].

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Scheme 16: Pd(0)-catalyzed C2- and C5-selective (hetero)arylation of ethyl oxazole-4-carboxylate [64].

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Scheme 17: Pd(0)-catalyzed direct C4-phenylation of oxazoles; (a) Miura’s procedure [65]; (b) Fagnou’s procedure [66].

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Scheme 18: Catalytic cycles for Cu(I)-catalyzed (routeA) and Pd(0)/Cu(I)-catalyzed (route B) direct arylation ...

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Scheme 19: Base-assisted, Pd(0)-catalyzed, C2-selective, direct arylation of benzoxazole proposed by Zhuralev [58]...

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Scheme 20: Electrophilic substitution-type mechanism proposed by Hoarau [64].

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Scheme 21: CMD-proceeding C5-selective direct arylation of oxazole proposed by Strotman and Chobabian [63].

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Scheme 22: DFT calculations on methyl oxazole-4-carboxylate and consequently developed methodologies for the P...

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Scheme 23: Pd(0)-catalyzed direct arylation of (benz)oxazoles with tosylates and mesylates [71].

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Scheme 24: Pd(0)-catalyzed direct arylation of oxazoles with sulfamates [72].

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Scheme 25: Pd(II)- and Cu(II)-catalyzed decarboxylative direct C–H coupling of oxazoles with 4- and 5-carboxyo...

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Scheme 26: Pd(II)- and Ag(II)-catalyzed decarboxylative direct arylation of (benzo)oxazoles [74]; (a) procedure; (...

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Scheme 27: Pd(II)- and Cu(II)-catalyzed direct arylation of benzoxazole with arylboronic acids [76]; (a) procedure...

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Scheme 28: Ni(II)-catalyzed direct arylation of benzoxazoles with arylboronic acids under O₂ [76]; (a) procedure; ...

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Scheme 29: Rhodium-catalyzed direct arylation of benzoxazole [78,79].

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Scheme 30: Ni(II)-catalyzed direct arylation of (benz)oxazoles with aryl halides; (a) Itami's procedure [80]; (b) ...

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Scheme 31: Dehydrogenative cross-coupling of (benz)oxazoles; (a) Pd(II)- and Cu(II)-catalyzed cross-coupling o...

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Review

Published 29 Nov 2011

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