https://pubs.rsc.org/en/content/articlepdf/2019/NP/C8NP00092A

Marine natural products.

/pdf/aryl-aryl-bond-formation-one-century-after-the-discovery-of-1jdyxlkwix.pdf

Aryl-aryl bond formation one century after the discovery of the Ullmann reaction.

The biaryl structural motif is a predominant feature in many pharmaceutically relevant and biologically active compounds. As a result, for over a century 1 organic chemists have sought to develop new and more efficient aryl -aryl bond-forming methods. Although there exist a variety of routes for the construction of aryl -aryl bonds, arguably the most common method is through the use of transition-metalmediated reactions. 2-4 While earlier reports focused on the use of stoichiometric quantities of a transition metal to carry out the desired transformation, modern methods of transitionmetal-catalyzed aryl -aryl coupling have focused on the development of high-yielding reactions achieved with excellent selectivity and high functional group tolerance under mild reaction conditions. Typically, these reactions involve either the coupling of an aryl halide or pseudohalide with an organometallic reagent (Scheme 1), or the homocoupling of two aryl halides or two organometallic reagents. Although a number of improvements have developed the former process into an industrially very useful and attractive method for the construction of aryl -aryl bonds, the need still exists for more efficient routes whereby the same outcome is accomplished, but with reduced waste and in fewer steps. In particular, the obligation to use coupling partners that are both activated is wasteful since it necessitates the installation and then subsequent disposal of stoichiometric activating agents. Furthermore, preparation of preactivated aryl substrates often requires several steps, which in itself can be a time-consuming and economically inefficient process.

http://aether.cmi.ua.ac.be/artikels/Artikels%20Gitte/Artikels/Reviews/Heck-Type-lautens.pdf

Aryl-aryl bond formation by transition-metal-catalyzed direct arylation.

/pdf/metal-organic-frameworks-and-self-assembled-supramolecular-2xs948xxr9.pdf

Metal–Organic Frameworks and Self-Assembled Supramolecular Coordination Complexes: Comparing and Contrasting the Design, Synthesis, and Functionality of Metal–Organic Materials

The direct functionalization of C-H bonds in organic compounds has recently emerged as a powerful and ideal method for the formation of carbon-carbon and carbon-heteroatom bonds. This Review provides an overview of C-H bond functionalization strategies for the rapid synthesis of biologically active compounds such as natural products and pharmaceutical targets.

C-H bond functionalization: emerging synthetic tools for natural products and pharmaceuticals

Figure Crystal structure of sphere 2b. Counterions and solvent are omitted for clarity. NW2/ 2003G186 Finite, Spherical Coordination Networks that Self-Organize from 36 Small Components Masahide Tominaga, Keisuke Suzuki, Masaki Kawano, Takahiro Kusukawa, Tomoji Ozeki, Shigeru Sakamoto, Kentaro Yamaguchi, and Makoto Fujita* 1 Department of Applied Chemistry, The University of Tokyo, CREST, Japan Science and Technology Corporation (JST), Bunkyo-ku, Tokyo 113-8656, Japan 2 Department of Chemistry and Materials Science. Tokyo Institute of Technology, Meguro-ku, Tokyo 152-8551, Japan 3 Chemical Analysis Center, Chiba University, Yayoi-cho, Inage-ku, Chiba 263-8522 (Japan)

Finite, Spherical Coordination Networks that Self‐Organize from 36 Small Components

Enantioface-differentiating (asymmetric) addition of alkyllithium and dialkylmagnesium to aldehydes by using (2S,2'S)-2-hydroxymethyl-1-[(1-alkylpyrrolidin-2-yl)methyl]pyrrolidines as chiral ligands

Catalytic enantioselective crossed aldehyde-ketone benzoin cyclization

Convergent total syntheses of the aryl C-glycoside antibiotics gilvocarcin M (1a) and gilvocarcin V (1b) have been accomplished. Key steps include (1) contrasteric coupling of D-fucofuranosyl acetate 27 with iodophenol 26, which was achieved by employing Cp 2 HfCl 2 -AgClO 4 or the related organosilane-derived reagents, and (2) regioselective [4+2] cycloaddition of a sugar-bearing benzyne species, generated by treatment of o-haloaryl triflate 33-α with n-BuLi at -78 o C, with 2-methoxyfuran (6). The naphthol derivative 34, selectively synthesized by these two tactics, served as the common intermediate to both 1a and 1b. Acylation of 34 with benzoic acid derivative 39 followed by Pd-catalyzed cyclization gave gilvocarcin M (1a), and a similar synthetic sequence starting with the coupling of 34 with 49 led to the first total synthesis of gilvocarcin V (1b)

Total synthesis of the gilvocarcins

New glycosidation reaction 1: Combinational use of Cp2ZrCl2-AgClO4 for activation of glycosyl fluorides and application to highly β-selective gylcosidation of D-mycinose

Keisuke Suzuki

Papers

Finite, Spherical Coordination Networks that Self‐Organize from 36 Small Components

Enantioface-differentiating (asymmetric) addition of alkyllithium and dialkylmagnesium to aldehydes by using (2S,2'S)-2-hydroxymethyl-1-[(1-alkylpyrrolidin-2-yl)methyl]pyrrolidines as chiral ligands

Catalytic enantioselective crossed aldehyde-ketone benzoin cyclization

Total synthesis of the gilvocarcins

New glycosidation reaction 1: Combinational use of Cp2ZrCl2-AgClO4 for activation of glycosyl fluorides and application to highly β-selective gylcosidation of D-mycinose