With Tag: General Organic Chemistry

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Intermolecular Hydroamination of Allenes with N-Unsubstituted Carbamates Catalyzed by a Gold(I) N-Heterocyclic Carbene Complex

Robert E. Kinder, Zhibin Zhang, Ross A. Widenhoefer
Org. Lett. | 2008 | 10.1021/ol8010858

Reaction of 2,3-pentadienyl benzoate with benzyl carbamate catalyzed by a 1:1 mixture of (NHC)AuCl and AgOTf in dioxane at 23 °C for 5 h led to isolation of (E)-4-(benzyloxycarbonylamino)-2-pentenyl benzoate in 84% yield as a single regio- and diastereomer....


Preparation of Potassium Alkoxymethyltrifluoroborates and Their Cross-Coupling with Aryl Chlorides

Gary A. Molander, Belgin Canturk
Org. Lett. | 2008 | 10.1021/ol800532p

A wide variety of alkoxymethyltrifluoroborate substrates were prepared via S N 2 displacement of potassium bromomethyltrifluoroborate with various alkoxides in excellent yields. These alkoxymethyltrifluoroborates were effectively cross-coupled with several...


Tin-Free Enantioselective Radical Reactions Using Silanes

Yong-Hua Yang, Mukund P. Sibi, Sunggi Lee
Org. Lett. | 2008 | 10.1021/ol802154d

Readily available hexyl silane is an excellent choice as a H-atom donor and a chain carrier in Lewis acid mediated enantioselective radical reactions. Conjugate radical additions to α,β-unsaturated imides at room temperature proceed in good yields and...


Highly Efficient Coupling of β-Substituted Aminoethane Sulfonyl Azides with Thio Acids, toward a New Chemical Ligation Reaction

Rob M. J. Liskamp, Remco Merkx, Arwin J. Brouwer, Dirk T. S. Rijkers
Org. Lett. | 2005 | 10.1021/ol0501119

A highly efficient coupling of protected β-substituted aminoethane sulfonyl azides with thio acids is reported. In the case of peptide thio acids, this method encompasses a new chemoselective ligation method. Furthermore, the resulting α-amino acyl...


Sequential Rh(I)/Pd-Catalyzed 1,4-Addition/Intramolecular Allylation:  Stereocontrolled Construction of γ-Butyrolactones and Cyclopropanes

Lauren G. Mercier, Sébastien Carret, Eric Fillion, Vincent É. Trépanier
Org. Lett. | 2008 | 10.1021/ol702613f

The rhodium-catalyzed conjugate addition of functionalized vinyltin reagents to alkylidene Meldrum's acids, followed by Pd-catalyzed intramolecular allylation, is a direct entry into vinyl-substituted γ-lactones via O-alkylation and vinylcyclopropanes via...


Engaging Zwitterions in Carbon−Carbon and Carbon−Nitrogen Bond-Forming Reactions:  A Promising Synthetic Strategy

A. R. Sreekanth, N. Abhilash, Rajeev S. Menon, A. T. Biju, Vijay Nair
Acc. Chem. Res. | 2006 | 10.1021/ar0502026

An Account of carbon−carbon and carbon−nitrogen bond-forming reactions mediated by zwitterions generated by the addition of organic nucleophiles to activated unsaturated systems highlighting their synthetic potential is presented.


Dehydrogenative Oxidation of Primary and Secondary Alcohols Catalyzed by a Cp*Ir Complex Having a Functional C,N-Chelate Ligand

Ken-ichi Fujita, Tetsuya Yoshida, Ryohei Yamaguchi, Yoichiro Imori
Org. Lett. | 2011 | 10.1021/ol2005424

A new catalytic system for the dehydrogenative oxidation of alcohols using a Cp*Ir complex having a functional C,N-chelate ligand has been developed. With this catalytic system, both primary and secondary alcohols were efficiently converted to aldehydes and...


A Simple, Nontoxic Iron System for the Allylation of Zinc Enolates

Silas P. Cook, Gopala K. Jarugumilli
Org. Lett. | 2011 | 10.1021/ol200059u

Diiron nonacarbonyl in combination with triphenylphosphine has been identified as a low-cost and environmentally benign catalyst system for the allylation of zinc enolates generated in situ from copper-catalyzed asymmetric conjugate addition reactions. The...


Iridium-Catalyzed X−H Insertions of Sulfoxonium Ylides

Ian K. Mangion, Mark A. Huffman, Michael Shevlin, Ikenna K. Nwamba
Org. Lett. | 2009 | 10.1021/ol901298p

The unique reactivity of sulfoxonium ylides as a carbene source is described for a variety of X−H bond insertions, taking advantage of a simple, commercially available iridium catalyst. This method has applications in both intra- and intermolecular...


Iridium-Catalyzed Coupling Reaction of Primary Alcohols with 1-Aryl-1-propynes Leading to Secondary Homoallylic Alcohols

Shintaro Hatanaka, Yasutaka Ishii, Yasushi Obora
Org. Lett. | 2009 | 10.1021/ol901366q

We report iridium-catalyzed coupling of 2-alkynes such as 1-aryl-1-propynes with primary alcohols leading to secondary homoallylic alcohols as products. This reaction involves an iridium-catalyzed novel catalytic transformation of 2-alkynes and primary...


New Catalytic Cycle for Couplings of Aldehydes with Organochromium Reagents

Kosuke Namba, Yoshito Kishi
Org. Lett. | 2004 | 10.1021/ol047661b

A new catalytic cycle has been developed to effect all three subgroups of Cr-mediated couplings, i.e., (1) Ni/Cr-mediated alkenylation, alkynylation, and arylation, (2) Co/Cr-mediated 2-haloallylation, alkylation, and propargylation, and (3) Cr-mediated...


Rh-Catalyzed Reductive Coupling Reaction of Aldehydes with Conjugated Dienes Promoted by Triethylborane

Masanari Kimura, Masahiro Fukushima, Yoshio Inoue, Yusuke Sonoda, Shuichi Oi, Daisuke Nojiri
Org. Lett. | 2009 | 10.1021/ol901527b

Rh(I) catalyzes the reductive coupling reaction of a wide variety of aldehydes with conjugated dienes in the presence of a stoichiometric amount of triethylborane to provide homoallyl alcohols in a single operation.


Silver-Catalyzed Difunctionalization of Terminal Alkynes: Highly Regio- and Stereoselective Synthesis of (Z)-β-Haloenol Acetates

Yibiao Li, Zhengwang Chen, Huanfeng Jiang, Shifa Zhu, Jinghao Li, Chaorong Qi
Org. Lett. | 2010 | 10.1021/ol101251n

A new silver-catalyzed highly regio- and stereoselective difunctionalization reaction of simple terminal alkynes was reported in which the (Z)-β-haloenol acetate derivatives were formed efficiently. The resulting products were versatile intermediates in...


A C–H Borylation Approach to Suzuki–Miyaura Coupling of Typically Unstable 2–Heteroaryl and Polyfluorophenyl Boronates

John F. Hartwig, Daniel W. Robbins
Org. Lett. | 2012 | 10.1021/ol301570t

A method for the synthesis of biaryls and heterobiaryls from arenes and haloarenes without the intermediacy of unstable boronic acids is described. Pinacol boronate esters that are analogous to unstable boronic acids are formed in high yield by...


Aminomethylations via Cross-Coupling of Potassium Organotrifluoroborates with Aryl Bromides

Deidre L. Sandrock, Gary A. Molander
Org. Lett. | 2007 | 10.1021/ol070543e

The Suzuki−Miyaura cross-coupling reaction of N,N-dialkylaminomethyltrifluoroborates with aryl halides allows the construction of an aminomethyl aryl linkage through a disconnection based on dissonant reactivity patterns. A variety of these...


Siloxyl Ether Functionalized Resins for Chemoselective Enrichment of Carboxylic Acids

Erin E. Carlson, Darci J. Trader
Org. Lett. | 2011 | 10.1021/ol202376m

Although the carboxylic acid moiety is prevalent in many biologically produced molecules, including natural products and proteins, methods to chemoselectively target this functional group have remained elusive. Generally, strategies that utilize carboxylate...


Selective Alkylation of Amines with Alcohols by Cp*–Iridium(III) Half-Sandwich Complexes

Frank Rominger, Mathias Schelwies, Marion K. Brinks, Michael Limbach, Simone Wöckel, Alexander Wetzel, Peter Hofmann
Org. Lett. | 2013 | 10.1021/ol303075h

[Cp*Ir(Pro)Cl] (Pro = prolinato) was identified among a series of Cp*–iridium half-sandwich complexes as a highly reactive and selective catalyst for the alkylation of amines with alcohols. It is active under mild conditions in either toluene or water without...


Tetra-ortho-Substituted Biaryls through Palladium-Catalyzed Suzuki−Miyaura Couplings with a Diaminochlorophosphine Ligand

Lutz Ackermann, Robert Born, Peter Mayer, Harish K. Potukuchi, Andreas Althammer
Org. Lett. | 2010 | 10.1021/ol1000186

A palladium complex derived from a sterically hindered diaminochlorophosphine allowed for Suzuki−Miyaura cross-couplings of chloroarenes with ample scope and provided access to tetra-ortho-substituted bi(hetero)aryls.


A Straightforward Protocol for One-Pot Allylic Aminations/Stille Couplings

Christian Bukovec, Uli Kazmaier
Org. Lett. | 2009 | 10.1021/ol901415p

Stannylated allylic carbonates are suitable substrates for Pd-catalyzed allylic aminations. In DMF and with [Pd(allyl)Cl] 2 as catalyst, the stannylated allyl amines formed can be directly coupled with electrophiles according to the Stille protocol, giving...


Arylsilanes: Application to Gold-Catalyzed Oxyarylation of Alkenes

Christopher A. Russell, Liam T. Ball, Michael Green, Guy C. Lloyd-Jones
Org. Lett. | 2010 | 10.1021/ol1019162

Arylsilanes are efficient reagents for the gold-catalyzed oxyarylation of alkenes (21 examples, up to 85% isolated yield). Using commercially available Ph 3 PAuCl and readily prepared, benign arylsilanes, these two- and three-component reactions proceed...

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