Oxidative Coupling between Two Hydrocarbons: An Update of Recent C–H Functionalizations

We thank the Spanish Ministerio de Ciencia e Innovacion (Grant Nos. CTQ2007-65218 and Consolider Ingenio 2010-CSD-2007-00006 and CTQ2011-24165), the Generalitat Valenciana (Grant No. PROMETEO/2009/039 and FEDER), and the University of Alicante for generous and continuous financial support.

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Diastereoselective allylation of carbonyl compounds and imines: application to the synthesis of natural products.

Encyclopedia Reagents in organic synthesis

An efficient Mn-catalyzed aerobic oxidative hydroxyazidation of olefins for synthesis of β-azido alcohols has been developed. The aerobic oxidative generation of azido radical employing air as the terminal oxidant is disclosed as the key process for this transformation. The reaction is appreciated by its broad substrate scope, inexpensive Mn-catalyst, high efficiency, easy operation under air, and mild conditions at room temperature. This chemistry provides a novel approach to high value-added β-azido alcohols, which are useful precursors of aziridines, β-amino alcohols, and other important N- and O-containing heterocyclic compounds. This chemistry also provides an unexpected approach to azido substituted cyclic peroxy alcohol esters. A DFT calculation indicates that Mn catalyst plays key dual roles as an efficient catalyst for the generation of azido radical and a stabilizer for peroxyl radical intermediate. Further calculation reasonably explains the proposed mechanism for the control of C-C bond cleavage or for the formation of β-azido alcohols.

Mn-Catalyzed Highly Efficient Aerobic Oxidative Hydroxyazidation of Olefins: A Direct Approach to β-Azido Alcohols

Mechanistic Manifold and New Developments of the Julia–Kocienski Reaction

Simple catalysts that use atom-economical oxygen as the terminal oxidant to accomplish selective ortho–ortho, ortho–para, or para–para homo-couplings of phenols are described. In addition, chromium salen catalysts have been discovered as uniquely effective in the cross-coupling of different phenols with high chemo- and regioselectivity.

Selective oxidative homo- and cross-coupling of phenols with aerobic catalysts.

(+)-SCH 351448 (Na+ salt A) was synthesized employing ring-closing olefin metathesis reaction of an open diene diester intermediate for construction of the 28-membered macrodiolide structure. The open diene diester was prepared from the monomeric hydroxy carboxylic acid and two different olefin fragments. The monomeric hydroxy acid was synthesized via Julia−Julia coupling reaction of intermediates derived from the same olefinic fragments. Oxane units in these fragments were prepared by radical cyclization reactions of β-alkoxyacrylates. Analogous SCH 351448 salts incorporating other mono- and divalent cations may be prepared. Under acidic conditions, SCH 351448 (Na+ salt A) was the most stable complex, but SCH 351448 (Ca2+ salt) and (Na+ salt B) appear to be physiologically important species.

Stereoselective Synthesis of (+)-SCH 351448: A Unique Ligand System for Sodium, Calcium, and Other Cations

Radical cyclization of vinylic ethers: expedient synthesis of (+)-monocerin.

Selective Oxidative Homo‐ and Cross‐Coupling of Phenols with Aerobic Catalysts.

Disclosed herein are improved methods for the synthesis of honokiol, as well as methods for the synthesis of 3,3'-di-tert-butyl-5,5'-dimethyl-[1,1'-biphenyl]-2,4'-diol, 3',5-dimethyl-[1,1'-biphenyl]-2,4'-diol, and 2,4'-dimethoxy-3',5-dimethyl-1,1'-biphenyl, 3,3',5,5'-tetra-tert-butyl-[1,1'-biphenyl]-2,4'-diol, and certain tetrasubstituted bisphenols, and uses therefor.

Young Eun Lee

Papers

Selective oxidative homo- and cross-coupling of phenols with aerobic catalysts.

Stereoselective Synthesis of (+)-SCH 351448: A Unique Ligand System for Sodium, Calcium, and Other Cations

Radical cyclization of vinylic ethers: expedient synthesis of (+)-monocerin.

Selective Oxidative Homo‐ and Cross‐Coupling of Phenols with Aerobic Catalysts.

Improved synthesis of honokiol