The selective functionalization of alkanes has long been recognized as a prominent challenge and an arduous task in organic synthesis. Hydrogen atom transfer (HAT) processes enable the direct generation of reactive alkyl radicals from feedstock alkanes and have been successfully employed in industrial applications such as the methane chlorination process, etc. Nevertheless, challenges in the regulation of radical generation and reaction pathways have created substantial obstacles in the development of diversified alkane functionalizations. In recent years, the application of photoredox catalysis has provided exciting opportunities for alkane C–H functionalization under extremely mild conditions to trigger HAT processes and achieve radical-mediated functionalizations in a more selective manner. Considerable efforts have been devoted to building more efficient and cost-effective photocatalytic systems for sustainable transformations. In this perspective, we highlight the recent development of photocatalytic systems and provide our views on current challenges and future opportunities in this field.

/pdf/resurgence-and-advancement-of-photochemical-hydrogen-atom-3mpr1ito.pdf

Resurgence and advancement of photochemical hydrogen atom transfer processes in selective alkane functionalizations

A practical, stereospecific direct amination of benzylic pinacol boronates was achieved by using aminoazanium of N-methyl morpholine (H2N-NMM) as a new amination reagent and cesium carbonate as the base. The in-situ reductive N-alkylation using aldehyde after amination was well performed to produce secondary amines.

Direct Amination of Benzylic Pinacol Boronates by an Aminoazanium

Photoredox Synthesis of
 Thio‐Functionalized
 Cyclic Ethers using
 
 N
 ‐Sulfenyl
 
 Phthalimides as a
 Thiyl‐Radical
 Precursor

The direct use of non-prefunctionalized arene and alkane as the starting materials to construct Caryl−Calkyl bond is an unfulfilled target and approaches to this challenge rarely surface in methodology studies. Current methods for thermocatalytic arene-alkane couplings (AAC) occur with specific substrates and/or inconvenient reagents. Herein, we report a one-pot relay bicatalysis system for AAC involving (pincer)Ir-catalyzed alkane transfer dehydrogenation and Fe(OTf)3-catalyzed olefin hydroarylation. This system exhibits broad scope and is particularly effective for alkylation of arenes with arylalkanes to form 1,1-diarylalkanes with high chemo- and regioselectivity, making it potentially useful for late-stage alkylation of complex molecules. Experimental mechanistic data provide a view into the factors controlling the regioselectivity. Finally, the strategy of dehydrogenation-enabled arene-alkane couplings has been successfully extended to a tandem catalysis by using a heterogeneous olefin hydroarylation catalyst. Appendix S1: Supporting Information Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article. 

Thermocatalytic <scp>Dehydrogenation‐Enabled Arene‐Alkane</scp> Couplings †

Thermal catalytic dehydrogenation of congested alkanes, such as the 1,1-disubstituted ethane (1,1-DSE) motif, is still a largely unsolved challenge. Herein, we report the investigation of biaryl-based atropisomeric diphosphines with various electronic and steric properties and their corresponding chloroiridium complexes for catalytic transfer dehydrogenation (CTD) of 1,1-DSEs using tert-butylethene as H-acceptor. The use of diphosphines of the biaryl backbone with a narrow dihedral angle was found to be essential to forming an effective catalytic species, cis-P2ClIr. A systematic investigation of three atropisomeric diphosphine classes, Segphos, MeO-Biphep, and Binap, revealed that the sterically hindered and electron-rich ligands are more efficient than the less hindered and electron-deficient ones. With an understanding of the structure–activity relationships, we developed two highly encumbered ligands 3,5-TMS,4-MeOMeO-Biphep (M12) and 3-TIPS,5-TMSMeO-Biphep (M13), which afforded >1400 turnovers at 150 °C in the cumene/TBE CTD reaction, representing the most efficient catalyst for thermal catalytic dehydrogenation of 1,1-DSEs. Moreover, these two ligands produced ∼420 turnovers in the CTD of 2-(1-adamantyl)propane, demonstrating their ability in dehydrogenation of unactivated hindered dialkyl-substituted ethanes. 

Chloroiridium Complexes of Biaryl-Based Diphosphines for Thermal Catalytic Transfer Dehydrogenation of Hindered 1,1-Disubstituted Ethanes

Dehydrogenation Based Asymmetric Epoxidation of Arylalkanes to Chiral Epoxides

Undirected, Asymmetric Alkyl Group Functionalizations through Alkane Dehydrogenation.

Oblivious transfer (OT) is one of the keystones of secure multi-party computation. It is generally believed that unconditionally secure OT is impossible. In this article, we propose a practical and secure quantum all-or-nothing oblivious transfer protocol based on the quantum one-way function. The protocol is built upon a quantum public-key encryption construction, and its security relies on the no-cloning theorem and no-communication theorem. Practical security is reflected in limitations on non-demolition measurements.

All-or-nothing oblivious transfer based on the quantum one-way function

. The relationship between complexity classes BQP and QMA is analogous to the relationship between P and NP. In this paper, we design a quantum bit commitment problem that is in QMA, but not in BQP. Therefore, it is proved that BQP ̸ = QMA. That is, problems that are verifiable in quantum polynomial time are not necessarily solvable in quantum polynomial time, the quantum analog of P ̸ = NP.

Bqp ̸ = qma

. Bit commitment (BC) is one of the most important fundamental protocols in secure multi-party computation. However, it is generally believed that unconditionally secure bit commitment is impossible even with quantum resources. In this paper, we design a secure non-interactive bit commitment protocol by exploiting the no-communication theorem of the quantum entangled states, whose security relies on the indistinguishability of whether the Bell states are measured or not. The proposed quantum bit commitment (QBC) is secure against classical adversaries with unlimited computing power, and the probability of a successful attack by quantum adversaries decreases exponentially as n (the number of qubits in a group) increases.

Secure Quantum Bit Commitment

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