Strain-release 2-azaallyl anion addition/borylation of [1.1.1]propellane: synthesis and functionalization of benzylamine bicyclo[1.1.1]pentyl boronates

Shelp, Russell A.; Ciro, Anthony; Pu, Youge; Merchant, Rohan R.; Hughes, Joseph V.; Walsh, Patrick J.

doi:10.1039/d1sc01349a

Cited by 41 publications

(24 citation statements)

References 40 publications

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“…Hughes and Walsh's group reported S-M couplings with various cyclic and bicyclic boron reagents 10.2 under Pd(OAc) 2 /cataCXium A (10) conditions (Scheme 9). 11 Similar to previous reports shown in this section, the desired coupling products 10.3a-d were obtained. Cu 2 O was also necessary to improve the yield of couplings.…”

Section: Scheme 8 Kanazawa and Uchiyama's Tert-alkylative S-m Couplingsupporting

confidence: 86%

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Tertiary Alkylative Suzuki–Miyaura Couplings

2022

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The Suzuki-Miyaura coupling is extremely useful to construct Csp2-Csp2 carbon bonds. On the other hand, Csp2-Csp3 coupling reactions are do not work well, and tert-alkylative Suzuki-Miyaura coupling is particularly challenging due to problematic oxidative addition and beta-hydride elimination side reactions. In this short review, we will introduce recent examples of tert-alkylative Suzuki-Miyaura couplings with tert-alkyl electrophiles or -boron reagents. The review will mainly focus on catalyst and product structures and the proposed mechanisms .

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Section: Scheme 8 Kanazawa and Uchiyama's Tert-alkylative S-m Couplingsupporting

confidence: 86%

“…Byers' group reported S-M couplings with tert-alkyl chlorides (Scheme 10). 12 In this case, an iron complex containing deprotonated cyanobis(oxazoline) ligand (11) was ef-…”

Section: Fe-catalyzed Tert-alkylative Couplingsmentioning

confidence: 99%

Tertiary Alkylative Suzuki–Miyaura Couplings

2022

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“…Additionally, Kanazawa, Uchiyama, and co-workers reported a Suzuki-type coupling using 1,3-difunctional silyl BCP boronates. Shortly after, the Walsh group, in collaboration with scientists at Merck, disclosed the use of 1,3-difunctional benzylamine BCP boronates in Suzuki couplings (Figure B).…”

mentioning

confidence: 99%

Nickel-Catalyzed Decarboxylative Cross-Coupling of Bicyclo[1.1.1]pentyl Radicals Enabled by Electron Donor–Acceptor Complex Photoactivation

et al. 2021

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The use of bicyclo[1.1.1]pentanes (BCPs) as para-disubstituted aryl bioisosteres has gained considerable momentum in drug development programs. Carbon–carbon bond formation via transition-metal-mediated cross-coupling represents an attractive strategy to generate BCP–aryl compounds for late-stage functionalization, but these typically require reactive organometallics to prepare BCP nucleophiles on demand from [1.1.1]propellane. In this study, the synthesis and Ni-catalyzed functionalization of BCP redox-active esters with (hetero)aryl bromides via the action of a photoactive electron donor–acceptor complex are reported.

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“…Indeed, an increasing demand from pharmaceutical institutions initiated many academic groups to work on elaboration of novel synthetic approaches to substituted bicyclo[1.1.1]pentanes and their analogues. − …”

Section: Introductionmentioning

confidence: 99%

Large-Scale Synthesis and Modifications of Bicyclo[1.1.1]pentane-1,3-dicarboxylic Acid (BCP)

et al. 2021

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In flow photochemical addition of propellane to diacetyl allowed construction of the bicyclo[1.1.1]pentane (BCP) core in a 1 kg scale within 1 day. Haloform reaction of the formed diketone in batch afforded bicyclo[1.1.1]pentane-1,3-dicarboxylic acid in a multigram amount. Representative gram scale transformations of the diacid were also performed to obtain various BCP-containing building blocks—alcohols, acids, amines, trifluoroborates, amino acids, etc .—for medicinal chemistry.

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Strain-release 2-azaallyl anion addition/borylation of [1.1.1]propellane: synthesis and functionalization of benzylamine bicyclo[1.1.1]pentyl boronates

Abstract: We report a 3-component reaction between N-benzyl ketimines, [1.1.1]propellane, and pinacol boronates to generate benzylamine bicyclo[1.1.1]pentane (BCP) pinacol boronates. These structures are analogous to highly sought after diarylmethanamine cores, which...

Cited by 41 publications

References 40 publications

Tertiary Alkylative Suzuki–Miyaura Couplings

Tertiary Alkylative Suzuki–Miyaura Couplings

Nickel-Catalyzed Decarboxylative Cross-Coupling of Bicyclo[1.1.1]pentyl Radicals Enabled by Electron Donor–Acceptor Complex Photoactivation

Large-Scale Synthesis and Modifications of Bicyclo[1.1.1]pentane-1,3-dicarboxylic Acid (BCP)

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