scholarly journals Spin-Center Shift-Enabled Direct Enantioselective α-Benzylation of Aldehydes with Alcohols

2018 ◽  
Vol 140 (9) ◽  
pp. 3322-3330 ◽  
Author(s):  
Eric D. Nacsa ◽  
David W. C. MacMillan
Keyword(s):  
ChemInform ◽  
2012 ◽  
Vol 43 (38) ◽  
pp. no-no
Author(s):  
Pablo Wessig
Keyword(s):  

2019 ◽  
Vol 5 (10) ◽  
pp. eaax9955 ◽  
Author(s):  
Jianyang Dong ◽  
Zhen Wang ◽  
Xiaochen Wang ◽  
Hongjian Song ◽  
Yuxiu Liu ◽  
...  

The polar nature of the C═O bond commonly allows it to undergo direct attack by nucleophiles at the electrophilic carbon atom in which ketones and aldehydes act as alkyl carbocation equivalents. In contrast, transformations in which ketones and aldehydes act as alkyl radical equivalents (generated in carbonyl carbon) are unknown. Here, we describe a new catalytic activation mode that combines proton-coupled electron transfer (PCET) with spin-center shift (SCS) and enables C─H alkylation of heteroarenes using ketones and aldehydes as alkyl radical equivalents. This transformation proceeded via reductive PCET activation of the ketones and aldehydes to form α-oxy radicals, addition of the radicals to the N-heteroarenes to form C─C bonds, and SCS to cleave the C─O bonds of the resulting alcohols. This mild protocol represents a general use of abundant, commercially available, ketones and aldehydes as latent alkyl radical equivalents.


2021 ◽  
Vol 143 (4) ◽  
pp. 1728-1734
Author(s):  
Gaoyuan Zhao ◽  
Wang Yao ◽  
Jaclyn N. Mauro ◽  
Ming-Yu Ngai

ChemInform ◽  
2007 ◽  
Vol 38 (32) ◽  
Author(s):  
Pablo Wessig ◽  
Olaf Muehling

2007 ◽  
Vol 2007 (14) ◽  
pp. 2219-2232 ◽  
Author(s):  
Pablo Wessig ◽  
Olaf Muehling

2012 ◽  
Vol 50 (1) ◽  
pp. 12-18 ◽  
Author(s):  
Su Shichuan ◽  
Wang Liang ◽  
Nie Yuhong ◽  
Gu Xiang

2021 ◽  
Vol 23 (1) ◽  
pp. 33-39
Author(s):  
Hyun-Jong Cho ◽  
◽  
Hyojin Kim

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