2-Alkylpyridines are a privileged scaffold throughout the realm of organic synthesis and play a key role in natural products, pharmaceuticals, and agrochemicals. Herein, we report the first B-alkyl Suzuki cross-coupling of 2-pyridyl ammonium salts to access functionalized 2-alkylpyridines. The use of well-defined, operationally simple Pd-NHCs permits for an exceptionally broad scope of the challenging B-alkyl C-N cross-coupling with organoboranes containing β-hydrogen, representing a novel method for the discovery of highly sought-after molecules for plant protection.
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Rapid and scalable photocatalytic C(sp)-C(sp) Suzuki-Miyaura cross-coupling of aryl bromides with alkyl boranes.
Nat Commun
May 2024
Flow Chemistry Group, van't Hoff Institute for Molecular Sciences (HIMS), University of Amsterdam, 1098, XH, Amsterdam, The Netherlands.
In recent years, there has been a growing demand for drug design approaches that incorporate a higher number of sp-hybridized carbons, necessitating the development of innovative cross-coupling strategies to reliably introduce aliphatic fragments. Here, we present a powerful approach for the light-mediated B-alkyl Suzuki-Miyaura cross-coupling between alkyl boranes and aryl bromides. Alkyl boranes were easily generated via hydroboration from readily available alkenes, exhibiting excellent regioselectivity and enabling the selective transfer of a diverse range of primary alkyl fragments onto the arene ring under photocatalytic conditions.
View Article and Find Full Text PDFAsymmetric Total Synthesis of (+)-Verrubenzospirolactone and (+)-Capillobenzopyranol.
Org Lett
April 2024
Department of Chemistry, Indian Institute of Technology-Kanpur, Kanpur 208016, India.
The first asymmetric total synthesis of (+)-verrubenzospirolactone (), a distinctive highly fused benzosesquiterpenoid, characterized by a pentacyclic skeletal structure, is realized through a concise 10-step synthetic pathway with an impressive 22.8% overall yield. Notable highlights of this synthetic endeavor include (i) the introduction of a Ru-catalyzed C-H activation step, (ii) the application of Pd-catalyzed asymmetric allylic alkylation to establish a pivotal stereocenter at C-3 with an excellent enantiomeric excess, (iii) -alkyl Suzuki-Miyaura coupling to construct a Diels-Alder precursor, and, ultimately, (iv) the successful deployment of an intramolecular Diels-Alder reaction to complete the synthesis of (+)-verrubenzospirolactone without erosion of the enantiomeric excess.
View Article and Find Full Text PDFRapid, Homogenous, B-Alkyl Suzuki-Miyaura Cross-Coupling of Boronic Esters.
J Org Chem
November 2024
Department of Chemistry, University of Illinois at Urbana-Champaign, 600 S. Matthews Ave, Urbana, Illinois 61801, United States.
A rapid, anhydrous Suzuki-Miyaura cross-coupling of alkylboronic esters with aryl halides is described. Parallel experimentation revealed that the combination of AntPhos, an oxaphosphole ligand, neopentyldiol alkylboronic esters, and potassium trimethylsilanolate (TMSOK) enables successful cross-coupling. In general, reactions proceed in under 1 h with good yields and high linear/branched (/) selectivities.
View Article and Find Full Text PDFPd-NHC (NHC = N-Heterocyclic Carbene)-Catalyzed B-Alkyl Suzuki Cross-Coupling of 2-Pyridyl Ammonium Salts by N-C Activation: Application to the Discovery of Agrochemical Molecular Hybrids.
Org Lett
March 2024
Department of Chemistry, Rutgers University, 73 Warren Street, Newark, New Jersey 07102, United States.
2-Alkylpyridines are a privileged scaffold throughout the realm of organic synthesis and play a key role in natural products, pharmaceuticals, and agrochemicals. Herein, we report the first B-alkyl Suzuki cross-coupling of 2-pyridyl ammonium salts to access functionalized 2-alkylpyridines. The use of well-defined, operationally simple Pd-NHCs permits for an exceptionally broad scope of the challenging B-alkyl C-N cross-coupling with organoboranes containing β-hydrogen, representing a novel method for the discovery of highly sought-after molecules for plant protection.
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RSC Adv
March 2023
Key Laboratory of Degraded and Unused Land Consolidation Engineering, The Ministry of Land and Resources of China, College of Environmental Science and Engineering, Chang'an University No. 126 Yanta Road Xi'an 710054 China.
We herein report α-arylsulfonyloxyacrylates as a kind of useful and attractive -centered electrophiles for Suzuki cross-coupling reactions. A range of α-(hetero)aryl substituted acrylates has been prepared the palladium-catalysed C-C cross-coupling reactions between potassium (hetero)aryltrifluoroborates and α-arylsulfonyloxyacrylates. Moreover, α-arylsulfonyloxyacrylate could also react with B-alkyl-9-BBN to produce α-alkyl substituted acrylates.
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