An operationally simple deaminative borylation reaction of primary alkylamines has been developed. The formation of electron-donor–acceptor complexes between N-alkylpyridinium salts and bis(catecholato)diboron enables photoinduced single-electron transfer and fragmentation to carbon-centered radicals, which are subsequently borylated. The mild conditions allow a diverse range of readily available alkylamines to be efficiently converted into synthetically valuable alkylboronic esters under catalyst-free conditions.

/pdf/photoinduced-deaminative-borylation-of-alkylamines-1j6o1e8qnm.pdf

Photoinduced Deaminative Borylation of Alkylamines

Triazine-based covalent organic polymers (COPs) constructed from triazine or nitrile containing precursors via covalent bonding are becoming an important sub-class of porous organic framework materials for a range of applications. In particular, these materials have been proposed as a new catalyst or support material for a variety of liquid phase organic transformation reactions owing to their tunable porous structures with high surface area, high nitrogen contents, high stability in both organic and aqueous media, and relatively easy synthesis. This review article summarizes the current research activities devoted to the synthesis and characterization of new triazine-based COP materials, and their applications for heterogeneous catalysis aiming at fine chemicals synthesis are presented with critical comments.

Triazine-based covalent organic polymers: design, synthesis and applications in heterogeneous catalysis

A deaminative strategy for the visible-light-mediated generation of alkyl radicals from redox-activated primary amine precursors is described. Abundant and inexpensive primary amine feedstocks, including amino acids, were converted in a single step into redox-active pyridinium salts and subsequently into alkyl radicals by reaction with an excited-state photocatalyst. The broad synthetic potential of this protocol was demonstrated by the alkylation of a number of heteroarenes under mild conditions.

/pdf/deaminative-strategy-for-the-visible-light-mediated-1lnzoiobk5.pdf

Deaminative Strategy for the Visible‐Light‐Mediated Generation of Alkyl Radicals

Carbon dioxide (CO2) is not only a greenhouse gas and a common waste product but also an inexpensive, readily available, and renewable carbon resource. It is an important one-carbon (C1) building block in organic synthesis for the construction of valuable compounds. However, its utilization is challenging owing to its thermodynamic stability and kinetic inertness. Although significant progress has been achieved, many limitations remain in this field with regard to the substrate scope, reaction system, and activation strategies.Since 2015, our group has focused on CO2 utilization in organic synthesis. We are also interested in the vast possibilities of radical chemistry, although the high reactivity of radicals presents challenges in controlling selectivity. We hope to develop highly useful CO2 transformations involving radicals by achieving a balance of reactivity and selectivity under mild reaction conditions. Over the past 6 years, we along with other experts have disclosed radical-type carboxylative cyclizations and carboxylations using CO2.We initiated our research by realizing the Cu-catalyzed radical-type oxytrifluoromethylation of allylamines and heteroaryl methylamines to generate valuable 2-oxazolidones with various radical precursors. Apart from Cu catalysis, visible-light photoredox catalysis is also a powerful method to achieve efficient carboxylative cyclization. In these cases, single-electron-oxidation-promoted C-O bond formation between benzylic radicals and carbamates is the key step.Since carboxylic acids exist widely in natural products and bioactive drugs and serve as important bulk chemicals in industry, we realized further visible-light-promoted carboxylations with CO2 to construct such chemicals. We have achieved the selective umpolung carboxylations of imines, enamides, tetraalkylammonium salts, and oxime esters by successive single-electron-transfer (SSET) reduction. Using this strategy, we have also realized the dearomative arylcarboxylation of indoles with CO2. In addition to the incorporation of 1 equiv of CO2 per substrate, we have recently developed a visible-light photoredox-catalyzed dicarboxylation of alkenes, allenes, and (hetero)arenes via SSET reduction, which allows the incorporation of two CO2 molecules into organic compounds to generate valuable diacids as polymer precursors.In addition to the two-electron activation of CO2, we sought to develop new strategies to realize efficient and selective transformations via single-electron activation of CO2. Inspired by the hypothetical electron-transfer mechanism of iron-sulfur proteins, we have realized the visible-light-driven thiocarboxylation of alkenes with CO2 using catalytic iron salts as promoters. The in-situ-generated Fe/S complexes are likely able to reduce CO2 to its radical anion, which could react with alkenes to give a stabilized carbon radical. Moreover, we have also disclosed charge-transfer complex (CTC) formation between thiolate and acrylate/styrene to realize the visible-light-driven hydrocarboxylation of alkenes with CO2 via generation of a CO2 or alkene radical anion. On the basis of this novel CTC, the visible-light-driven organocatalytic hydrocarboxylation of alkenes with CO2 has also been realized using a Hantzsch ester as an effective reductant.

Radical Carboxylative Cyclizations and Carboxylations with CO2

Organoborons have emerged as versatile building blocks in organic synthesis to achieve molecular diversity and as carboxylic acid bioisosteres with broad applicability in drug discovery Traditiona

Methodologies and Strategies for Selective Borylation of C–Het and C–C Bonds

Transition-metal catalysed C–N bond activation has attracted much attention and become one of the most promising bond disconnection and formation strategies that encompass a broad spectrum of applications in many reactions. In this tutorial review, efficient strategies for catalytic cleavage of C(sp)–N, C(sp2)–N and C(sp3)–N bonds and their applications in new C–C and C–N bond formation reactions are summarized.

/pdf/transition-metal-catalysed-c-n-bond-activation-1r8ryjv4of.pdf

Transition-metal catalysed C–N bond activation

Transition‐Metal Catalyzed C—N Bond Activation

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Transition-metal catalysed C–N bond activation

Transition‐Metal Catalyzed C—N Bond Activation