Latest Articles of The Journal of Organic Chemistry


Synthesis and Unique Optical Properties of Selenophenyl BODIPYs and Their Linear Oligomers 10.1021/acs.joc.8b00782 2018-04-19 A series of selenophene-substituted boron-dipyrrin (BODIPY) monomers and selenophene-linked BODIPY oligomers was synthesized. The synthesized BODIPYs show good absorption/emission properties in the red to near-infrared region. Furthermore, some of the selenop...
Synthesis of 3,5-Disubstituted BODIPYs Bearing N-Containing Five-Membered Heteroaryl Groups via Nucleophilic C–N Bond Formation 10.1021/acs.joc.8b00087 2018-04-17 Aromatic substitution reactions were applied to the divergent synthesis of a series of symmetrically and unsymmetrically 3,5-disubstituted BODIPYs bearing N-heteroaryl groups. Furthermore, the effect of N-heteroaryl substituents at the 3- and 5-positions on t...
Steric Hindrance Underestimated: It is a Long, Long Way to Tri-tert-alkylamines 10.1021/acs.joc.8b00496 2018-04-17 Ten different processes (Methods A–J) were tested to prepare tertiary amines bearing bulky alkyl groups. In particular, SN1 alkylation of secondary amines with the help of 1-adamantyl triflate (Method D) and reaction of N-chlorodialkylamines with organometall...
Stereoselective Sequential [4+2]/[2+2] Cycloadditions Involving 2-Alkenylindolenines: An Approach to Densely Functionalized Benzo[b]indolizidines 10.1021/acs.joc.8b00346 2018-04-16 A stereoselective sequential [4+2]/[2+2] cycloaddition process involving 2-alkenylindolenines has been developed. This unprecedented protocol allows a rapid access to densely functionalized benzo[b]indolizidines containing a fully substituted piperidine ring ...
Pd-Induced Double C–H Bond Activation in Annulative Syntheses of Bipyrrole Boomerangs: Mechanistic Insights from NMR Spectroscopy and Computation 10.1021/acs.joc.8b00630 2018-04-16 1,n-Dipyrrolylalkanes can be efficiently converted into extensively π-conjugated bipyrroles by PdII-mediated annulative double C–H activation, and this approach might be further developed into tandem processes involving further cyclization of substituents or ...
DiCE: Diastereomeric in Silico Chiral Elucidation, Expanded DP4 Probability Theory Method for Diastereomer and Structural Assignment 10.1021/acs.joc.8b00338 2018-04-16 NMR chemical shift prediction at the B3LYP/cc-pVDZ level of theory was used to develop a highly accurate probability theory algorithm for the determination of the stereochemistry of diastereomers as well as the regiochemistry. DFT-GIAO calculations were perfo...
Synthesis and Evaluation of Antibacterial Activity of Bottromycins 10.1021/acs.joc.8b00045 2018-04-16 Total synthesis of bottromycin A2 can be accomplished through a diastereoselective Mannich reaction of a chiral sulfinamide, mercury-mediated intermolecular amidination, and cyclization of a constrained tetracyclic peptide. Exploitation of this process allowe...
Tn Antigen Mimics by Ring-Opening of Chiral Cyclic Sulfamidates with Carbohydrate C1-S- and C1-O-Nucleophiles 10.1021/acs.joc.7b03225 2018-04-13 Starting from commercially available (S)-isoserine and effectively accessible (S)-α-methylserine, enantiopure cyclic sulfamidates have been prepared as chiral building blocks for the synthesis of various S- and O-glycosylated amino acid derivatives, including...
Synthesis of 1-Cyanoalkynes and Their Ruthenium(II)-Catalyzed Cycloaddition with Organic Azides to Afford 4-Cyano-1,2,3-triazoles 10.1021/acs.joc.8b00424 2018-04-13 A new method to convert terminal alkynes under relatively mild conditions to 1-cyanoalkynes using in situ formed cyanogen is described. 1-Cyanoalkynes have a higher reactivity than terminal alkynes in the ruthenium(II)-catalyzed regiospecific azide–alkyne cyc...
Improved Substrate Scope in the Potassium Hexacyanoferrate(II)-Based Cyanation for the Synthesis of Benzonitriles and Their Heterocyclic Analogues 10.1021/acs.joc.8b00515 2018-04-12 The use of Pd(DPEPhos)Cl2 (P26) as a catalyst for the formation of benzonitriles and their heterocyclic analogues provides excellent complementarity to existing catalysts, allowing highly electron-deficient heterocyclic aryl halides to be efficiently converte...

Synthesis and Unique Optical Properties of Selenophenyl BODIPYs and Their Linear Oligomers

10.1021/acs.joc.8b00782

2018-04-19

A series of selenophene-substituted boron-dipyrrin (BODIPY) monomers and selenophene-linked BODIPY oligomers was synthesized. The synthesized BODIPYs show good absorption/emission properties in the red to near-infrared region. Furthermore, some of the selenop...

Synthesis of 3,5-Disubstituted BODIPYs Bearing N-Containing Five-Membered Heteroaryl Groups via Nucleophilic C–N Bond Formation

10.1021/acs.joc.8b00087

2018-04-17

Aromatic substitution reactions were applied to the divergent synthesis of a series of symmetrically and unsymmetrically 3,5-disubstituted BODIPYs bearing N-heteroaryl groups. Furthermore, the effect of N-heteroaryl substituents at the 3- and 5-positions on t...

Steric Hindrance Underestimated: It is a Long, Long Way to Tri-tert-alkylamines

10.1021/acs.joc.8b00496

2018-04-17

Ten different processes (Methods A–J) were tested to prepare tertiary amines bearing bulky alkyl groups. In particular, SN1 alkylation of secondary amines with the help of 1-adamantyl triflate (Method D) and reaction of N-chlorodialkylamines with organometall...

Stereoselective Sequential [4+2]/[2+2] Cycloadditions Involving 2-Alkenylindolenines: An Approach to Densely Functionalized Benzo[b]indolizidines

10.1021/acs.joc.8b00346

2018-04-16

A stereoselective sequential [4+2]/[2+2] cycloaddition process involving 2-alkenylindolenines has been developed. This unprecedented protocol allows a rapid access to densely functionalized benzo[b]indolizidines containing a fully substituted piperidine ring ...

Pd-Induced Double C–H Bond Activation in Annulative Syntheses of Bipyrrole Boomerangs: Mechanistic Insights from NMR Spectroscopy and Computation

10.1021/acs.joc.8b00630

2018-04-16

1,n-Dipyrrolylalkanes can be efficiently converted into extensively π-conjugated bipyrroles by PdII-mediated annulative double C–H activation, and this approach might be further developed into tandem processes involving further cyclization of substituents or ...

DiCE: Diastereomeric in Silico Chiral Elucidation, Expanded DP4 Probability Theory Method for Diastereomer and Structural Assignment

10.1021/acs.joc.8b00338

2018-04-16

NMR chemical shift prediction at the B3LYP/cc-pVDZ level of theory was used to develop a highly accurate probability theory algorithm for the determination of the stereochemistry of diastereomers as well as the regiochemistry. DFT-GIAO calculations were perfo...

Synthesis and Evaluation of Antibacterial Activity of Bottromycins

10.1021/acs.joc.8b00045

2018-04-16

Total synthesis of bottromycin A2 can be accomplished through a diastereoselective Mannich reaction of a chiral sulfinamide, mercury-mediated intermolecular amidination, and cyclization of a constrained tetracyclic peptide. Exploitation of this process allowe...

Tn Antigen Mimics by Ring-Opening of Chiral Cyclic Sulfamidates with Carbohydrate C1-S- and C1-O-Nucleophiles

10.1021/acs.joc.7b03225

2018-04-13

Starting from commercially available (S)-isoserine and effectively accessible (S)-α-methylserine, enantiopure cyclic sulfamidates have been prepared as chiral building blocks for the synthesis of various S- and O-glycosylated amino acid derivatives, including...

Synthesis of 1-Cyanoalkynes and Their Ruthenium(II)-Catalyzed Cycloaddition with Organic Azides to Afford 4-Cyano-1,2,3-triazoles

10.1021/acs.joc.8b00424

2018-04-13

A new method to convert terminal alkynes under relatively mild conditions to 1-cyanoalkynes using in situ formed cyanogen is described. 1-Cyanoalkynes have a higher reactivity than terminal alkynes in the ruthenium(II)-catalyzed regiospecific azide–alkyne cyc...

Improved Substrate Scope in the Potassium Hexacyanoferrate(II)-Based Cyanation for the Synthesis of Benzonitriles and Their Heterocyclic Analogues

10.1021/acs.joc.8b00515

2018-04-12

The use of Pd(DPEPhos)Cl2 (P26) as a catalyst for the formation of benzonitriles and their heterocyclic analogues provides excellent complementarity to existing catalysts, allowing highly electron-deficient heterocyclic aryl halides to be efficiently converte...