Trifluoromethyltrimethylsilane: nucleophilic trifluoromethylation and beyond.

Carbon-sulfur bond cross-coupling has become more and more attractive as an alternative protocol to establish carbon-carbon and carbon-heteroatom bonds. Diverse transformations through transition-metal-catalyzed C-S bond activation and cleavage have recently been developed. This review summarizes the advances in transition-metal-catalyzed cross-coupling via carbon-sulfur bond activation and cleavage since late 2012 as an update of the critical review on the same topic published in early 2013 (Chem. Soc. Rev., 2013, 42, 599-621), which is presented by the categories of organosulfur compounds, that is, thioesters, thioethers including heteroaryl, aryl, vinyl, alkyl, and alkynyl sulfides, ketene dithioacetals, sulfoxides including DMSO, sulfones, sulfonyl chlorides, sulfinates, thiocyanates, sulfonium salts, sulfonyl hydrazides, sulfonates, thiophene-based compounds, and C[double bond, length as m-dash]S functionality-bearing compounds such as thioureas, thioamides, and carbon disulfide, as well as the mechanistic insights. An overview of C-S bond cleavage reactions with stoichiometric transition-metal reagents is briefly given. Theoretical studies on the reactivity of carbon-sulfur bonds by DFT calculations are also discussed.

Transition-metal mediated carbon-sulfur bond activation and transformations: an update.

Quinoline is one of the most widely investigated scaffolds by synthetic chemists because of its medicinal importance. A wide range of metal-catalyzed, metal-free, multi-step or domino one-pot protocols are reported in the literature for construction of this scaffold. Several reviews have appeared on synthetic aspects of this scaffold, however there is no focused review on metal-free domino one-pot protocols. Domino one-pot protocols offer an opportunity to access highly functionalized final products from simple starting materials. Because of this unique feature of domino protocols, in recent years their utility for generation of molecular libraries has been widely appreciated. In this review, all contributions till March 2015 are surveyed with particular emphasis on metal-free domino reactions for quinoline ring construction and are discussed herein along with mechanistic aspects.

Metal-free domino one-pot protocols for quinoline synthesis

Push–pull alkenes, which bear electron-donating and -accepting group(s) at both termini of a C═C double bond, respectively, are of interest not only for their unique electronic properties but also for their importance as versatile building blocks in organic synthesis. In the world of ketene acetals having the push–pull alkene skeleton, ketene N,S-acetal is most likely the biggest family according to the number and types of these compounds. The first ketene N,S-acetal compound was reported in 1956. As a cyclic ketene N,S-acetal compound, nithiazine, the first lead structure of neonicotinoid insecticides, was reported in 1978. The characteristics of ketene N,S-acetals, which have the structural feature of ketene S,S-acetals and enaminones, make them versatile and easy to use, especially in cyclization and multicomponent reactions for the synthesis of various heterocyclic systems and related natural products. There has been an increasing wealth of information about the synthesis and synthetic applications of...

Chemistry of Ketene N,S-Acetals: An Overview.

Chemoselective cross-coupling reaction of sodium sulfinates with phenols under aqueous conditions

Ketene dithioacetals are versatile intermediates in organic synthesis. Extensive research, since the last decade, has given rise to new prospects in their chemistry. The objective of this review is twofold: first, to highlight the new prospects in the chemistry of functionalized ketene dithioacetals, and second, to provide an intrinsic link between ketene dithioacetal groups and a variety of other functional groups, which has brought out many new facts that will assist in future designs.

Ling Pan

Papers

Recent developments of ketene dithioacetal chemistry.

Recent Developments of Ketene Dithioacetal Chemistry