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Archive for the ‘Hypervalent Iodine’ Category

Triiodide-mediated C-H amination

Posted by naturalproductman on July 31, 2016

David Nagib and co-workers from the Ohio State University have reported in ACIE on a triiodide mediated C-H amination reaction.

 

ACIE paper

Posted in C-H activation, Hypervalent Iodine, Methodology | Leave a Comment »

Olefin difluorinations are in

Posted by naturalproductman on April 7, 2016

Ryan Gilmour and colleague at Westfal̈ische Wilhelms-Universitaẗ Münster have reported in JACS on a difluorination of an olefin using p-iodotoluene, selectfluor, and various sources of amine-HF including TREAT-HF (triethylamine trihydrofluoride). They also try to expand on the transformation by making it asymmetric using a C2-symmetric chiral aryl iodide.

 

JACS paper

Posted in Hypervalent Iodine, Methodology | Leave a Comment »

Olefin difluorination

Posted by naturalproductman on April 5, 2016

Eric Jacobsen and co-workers reported in JACS on a difluorination of an olefin. They accomplished this transformation by using mCPBA (1.1 equivalent), HF-pyridine (100 equivalents of HF), and an aryl iodide derivative (catalyst).

 

JACS paper

Posted in Hypervalent Iodine, Mechanistic, Methodology | Leave a Comment »

α-Aminations via Nitrenoids

Posted by naturalproductman on February 24, 2016

Takashi Ohshima and co-workers from Kyushu University reported in JACS on the use of hypervalent iodine to perform an N-H insertion

 

 

JACS paper

Posted in C-H activation, Hypervalent Iodine, Methodology, Nitrene | Leave a Comment »

2 Reagents, 2 mechanisms, same product

Posted by naturalproductman on January 28, 2016

Srinivasan Chandrasekaran and colleague at the Indian Institute of Science have reported in Tetrahedron on a mechanistically interesting transformation involving a geminal aminooxygenation of a vinyl arene. Two different reaction conditions were identified: one with m-CPBA, the other with a hypervalent iodine reagent. The former underwent a deuterium shift on the gem-dideuterated-styrene starting material and the latter does not.

01.28.2016 naturalproductman.gif

Tetrahedron paper

Posted in Cascade Reactions, Hypervalent Iodine, Mechanistic, Methodology | Leave a Comment »

ACIE Journals of Interest 11/24/2015

Posted by naturalproductman on November 24, 2015

Hao Xu’s lab in University of Georgia have reported on an iron-catalyzed diazidation of olefins.

Dorian Didier’s lab from LMU Munich reported on an interesting one-pot reaction.

Xiaoguang Lei’s lab from Peking University reported on the structural revision of aspergillomarasmine A.

Kilian Muniz’s lab from ICIQ reported on a hypervalent iodine approach to form 1,2-diacetates from olefins, asymmetrically.

NATURALPRODUCTMAN11.24.2015

Posted in Cascade Reactions, Hypervalent Iodine, Methodology, Structural Reassignment, Total Synthesis | Leave a Comment »

Radical cascade using hypervalent iodine

Posted by naturalproductman on October 1, 2015

Xin-Hua Duan and co-workers from Xi’an Jiaotong University have reported in Organic Letters on a hypervalent iodine approach to accessing alkynylated ketones.
alkylation

OL paper

Posted in Cascade Reactions, Hypervalent Iodine, Methodology | Leave a Comment »

Syn-1,3-carbonate access

Posted by naturalproductman on May 28, 2015

Matthew Gaunt and colleague at the University of Cambridge have reported in ACIE on a method for the synthesis of syn-1,3-carbonates.

Cu

ACIE paper

Posted in Copper, Hypervalent Iodine, Methodology, Transition Metal | Leave a Comment »

Hypervalent iodine towards lactams

Posted by naturalproductman on May 2, 2015

Antonio Herrera and co-workers from CSIC have reported in Organic Letters on a hypervalent iodine approach to access lactams from linear precursors.

OL paper

Posted in Hofmann–Löffler–Freytag-type, Hypervalent Iodine, Methodology, Named Reactions | Leave a Comment »

Trifluoromethylation with hypervalent iodine

Posted by naturalproductman on April 12, 2015

Mikiko Sodeoka and co-workers from RIKEN have reported in JACS on a aminotrifluoromethylation of olefins using a hypervalent iodine reagent.
iodine

JACS paper

Posted in Hypervalent Iodine, Methodology | Leave a Comment »