Tuneable access to isoquinolines via a transition-metal-free C(sp3)–C(sp3) bond cleavage rearrangement reaction

2019 ◽  
Vol 6 (14) ◽  
pp. 2430-2434 ◽  
Author(s):  
Jian Wang ◽  
Panyuan Cai ◽  
Yimiao He ◽  
Yuan Liu ◽  
Ling Zhong ◽  
...  

A novel divergent synthesis of multi-substituted isoquinolines via C(sp3)–C(sp3) bond cleavage rearrangement reactions was realized.

Molecules ◽  
2019 ◽  
Vol 24 (3) ◽  
pp. 459 ◽  
Author(s):  
Hengzhao Li ◽  
Zemin Lai ◽  
Adila Adijiang ◽  
Hongye Zhao ◽  
Jie An

Functionalization of amide bond via the cleavage of a non-carbonyl, C-N σ bond remains under-investigated. In this work, a transition-metal-free single-electron transfer reaction has been developed for the C-N σ bond cleavage of N-acylazetidines using the electride derived from sodium dispersions and 15-crown-5. Of note, less strained cyclic amides and acyclic amides are stable under the reaction conditions, which features the excellent chemoselectivity of the reaction. This method is amenable to a range of unhindered and sterically encumbered azetidinyl amides.


2019 ◽  
Vol 43 (11-12) ◽  
pp. 486-492
Author(s):  
Jiasi Tao ◽  
Weijie Yu ◽  
Jin Luo ◽  
Tao Wang ◽  
Wanling Ge ◽  
...  

A mild, efficient, and transition-metal-free catalytic strategy is developed to construct thioesters via selective N–C bond cleavage of Boc2-activated primary amides. This strategy is successfully carried out with stoichiometric Na2CO3 as the base and provides the corresponding products in moderate to excellent yields.


2020 ◽  
Vol 11 (22) ◽  
pp. 5740-5744 ◽  
Author(s):  
Qian Dou ◽  
Chao-Jun Li ◽  
Huiying Zeng

“We report a protocol for photoinduced transition-metal- and external-photocatalyst-free intramolecular heteroaryl/aryl rearrangement reactions of 2-heteroaryl/aryloxybenzaldehydes. The protocol was compatible with a variety of functionalities.


2020 ◽  
Vol 56 (58) ◽  
pp. 8143-8146
Author(s):  
Murugan Subaramanian ◽  
Palmurukan M. Ramar ◽  
Jagannath Rana ◽  
Virendra Kumar Gupta ◽  
Ekambaram Balaraman

The catalytic conversion of ketones to esters via C(O)–C bond cleavage under transition-metal free conditions is reported.


2012 ◽  
Vol 85 (4) ◽  
pp. 829-834 ◽  
Author(s):  
Vitaly Nesterov ◽  
Tobias Heurich ◽  
Rainer Streubel

An approach to novel P-functional chloroformylphosphane complexes is described using the synthetic potential of lithium/halogeno phosphinidenoid tungsten(0) complexes. Similarly to transition-metal-free chloroformylphosphanes, the obtained complexes tend to eliminate CO via P–C bond cleavage to give the corresponding P-chlorophosphane complex derivatives. Nevertheless, this method allowed the isolation of the first complex derivatives, which will open new synthetic perspectives in organophosphorus chemistry.


RSC Advances ◽  
2016 ◽  
Vol 6 (89) ◽  
pp. 86464-86467 ◽  
Author(s):  
Zhengwang Chen ◽  
Yuelu Wen ◽  
Guotian Luo ◽  
Min Ye ◽  
Qinghao Wang

A highly efficient transition-metal-free cyclization reaction for the synthesis of 2,3-diarylimidazo[1,2-α]pyridines is described.


2018 ◽  
Vol 54 (79) ◽  
pp. 11148-11151 ◽  
Author(s):  
Lian-Hua Li ◽  
Zhi-Jie Niu ◽  
Ying-Xiu Li ◽  
Yong-Min Liang

A metal-free brand-new one-pot multinitrogenation of amides for the chemo-, regioselective synthesis of 1,5-disubstituted tetrazoles has been developed.


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