The Suzuki-Miyaura cross coupling reactions on solid support. Link to solution phase directed ortho metalation. The Leznoff acetal linker approach to biaryl and heterobiaryl aldehydes

Chamoin, Sylvie; Houldsworth, Stephen J.; Kruse, Chris G.; Bakker, Wouter; Snieckus, Victor

doi:10.1016/s0040-4039(98)00779-5

Cited by 63 publications

(26 citation statements)

References 9 publications

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“…12 This synthetic methodology is outlined in Scheme 1. Under the conditions utilized, the formation of a carbon-carbon bond between the bromobenzaldehyde and aminophenyl boronic acid occurred, followed by an in situ intramolecular Schiff base formation to yield the neutral phenanthridines 11-13 in good yields.…”

Section: Synthesismentioning

confidence: 99%

Structure−Activity Relationship Studies of Phenanthridine-Based Bcl-X_L Inhibitors

et al. 2008

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Despite their structural similarities, the natural products chelerythrine ( 5) and sanguinarine ( 6) target different binding sites on the pro-survival Bcl-X L protein. This paper details the synthesis of phenanthridine-based analogues of the natural products that were used to probe this difference in binding profiles. The inhibitory constants for these compounds were then measured in a fluorescence polarization assay against Bcl-X L and the tagged Bak-BH3 peptide. The results led to structure-activity relationship studies, which identified the structural motifs required for binding-site specificity as well as inhibitory activity. We also identified synthetic analogues of the natural products that display similar binding modes but with more potent IC 50 values.

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Section: Synthesismentioning

confidence: 99%

Structure−Activity Relationship Studies of Phenanthridine-Based Bcl-X_L Inhibitors

et al. 2008

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“…Similar processes are increasingly being used for the construction of polyaryls of interest in material science areas [51]. The Suzuki-Miyaura tactic carried out on solid support (Scheme 28) [52] provides routes to small libraries of condensed heterocycles. Thus, Merrifield resin with the Leznoff-linked bromobenzene derivative 78 undergoes cross-coupling under normal solution-phase conditions with boron pinacolate 79 or boronic acid 80, prepared by DoM, to afford phenanthridines 81 or, via 82 and some manipulation, dibenzopyranones 83 in good yields and with high purities.…”

Section: 41mentioning

confidence: 99%

The Directed ortho Metalation Reaction – A Point of Departure for New Synthetic Aromatic Chemistry

Hartung

Snieckus

2002

Modern Arene Chemistry

159

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After a brief allusion to the current status of synthetic aromatic chemistry, a tour based on the Directed ortho Metalation (DoM) strategy is provided with selections from recent literature which highlight a) the use of DoM for the regiospecific preparation of polysubstituted aromatics and heteroaromatics; b) the valuable symbiosis of DoM with transition metal catalyzed AraAr cross-coupling protocols; c) the extension of DoM to the Directed remote Metalation (DreM) concept in biaryls, which provides methodologies for the construction of condensed aromatics (fluorenones, phenanthrols) and heterocyclics (thioxanthones, xanthones, acridones, dibenzphosphorinones, dibenzthiepinone dioxides, dibenzoxepinones, dibenzazepinones, dibenzphosphinones); and d) the evolving links of DoM to other modern methodologies with a note on the DoM-Grubbs ring-closing metathesis connection. The presentation is solely methodologically rather than total synthesis oriented; dependable directed metalation groups (DMGs ¼ CONR 2 , OCONR 2 , SONR 2 , NHBoc), new and renewed, are emphasized; p-excessive (furan, thiophene, indole) and p-deficient (pyridine) heterocycle HetDoM chemistry is delineated. While definitely not comprehensive, this account attempts to give a flavor of current anionic aromatic chemistry in synthesis. 10.1Scheme 1. Synthetic approaches to substituted aromatics. 10.2 The DoM Reaction as a Methodological Tool 331 Scheme 3. DoM chemistry generalizations. 10.2 The DoM Reaction as a Methodological Tool 333 Scheme 5. The N-cumyl sulfonamide DMG. Scheme 6. The N-cumyl carbamate DMG. 10.2 The DoM Reaction as a Methodological Tool 335 Scheme 9. The di-tert-butyl phosphine oxide DMG. 10.3 Heteroaromatic Directed ortho Metalation (HetDoM) in Methodological Practice 337

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“…In these cases the ligand molecules associate themselves spontaneously with the air-stable Pd salt if co-solvated in an appropriate solvent. Various bases have been used as co-catalysts, among them KOH [43], Na 2 CO 3 [7,15], K 2 CO 3 [8,9,44], KHCO 3 [44], Ba(OH) 2 [29], NEt 3 , CsF [45,46], KF [8], and K 3 PO 4 [6,8,20,21,24]. Unfortunately their impact on the yield of a given coupling and the purity of the final products are difficult to estimate [47].…”

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confidence: 99%

“…The use of air-stable Pd sources such as Pd 2 (dba) 3 , Pd(dppf)Cl 2 , and Pd(OAc) 2 , allows the preparation of mixtures of bulk dry boronic acid ground together in the appropriate ratio with the Pd catalyst. These mixtures of solids can then be distrib- Merrifield [95] Br Ph, Ph with EDG in 2-and 3-positions, 3-thiophenyl, 2-thiophenyl 0.05 equiv. Pd(PPh3) 4 Boronate resin [55] REM resin [121] Ph with EWG and EDG in 2, 3, 4 position 4 equiv.…”

mentioning

confidence: 99%

CC Bond‐Forming Reactions

Brill¹,

Papeo²

2006

Combinatorial Chemistry

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The Suzuki-Miyaura cross coupling reactions on solid support. Link to solution phase directed ortho metalation. The Leznoff acetal linker approach to biaryl and heterobiaryl aldehydes

Cited by 63 publications

References 9 publications

Structure−Activity Relationship Studies of Phenanthridine-Based Bcl-X_L Inhibitors

Structure−Activity Relationship Studies of Phenanthridine-Based Bcl-X_L Inhibitors

The Directed ortho Metalation Reaction – A Point of Departure for New Synthetic Aromatic Chemistry

CC Bond‐Forming Reactions

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The Suzuki-Miyaura cross coupling reactions on solid support. Link to solution phase directed ortho metalation. The Leznoff acetal linker approach to biaryl and heterobiaryl aldehydes

Cited by 63 publications

References 9 publications

Structure−Activity Relationship Studies of Phenanthridine-Based Bcl-XL Inhibitors

Structure−Activity Relationship Studies of Phenanthridine-Based Bcl-XL Inhibitors

The Directed ortho Metalation Reaction – A Point of Departure for New Synthetic Aromatic Chemistry

CC Bond‐Forming Reactions

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Structure−Activity Relationship Studies of Phenanthridine-Based Bcl-X_L Inhibitors

Structure−Activity Relationship Studies of Phenanthridine-Based Bcl-X_L Inhibitors