TY - JOUR
T1 - Catalyst-Dependent Direct and Deoxygenative Coupling of Alcohols by Convergent Paired Electrolysis
AU - Zhang, Sheng
AU - Shi, Jianxue
AU - Li, Jingjing
AU - Li, Man Bo
AU - Li, Guigen
AU - Findlater, Michael
N1 - Publisher Copyright:
© 2022 CCS Chemistry. All rights reserved.
PY - 2022/6
Y1 - 2022/6
N2 - Developing a general and mild approach to upgrade alcohols into high value products is a hot topic in synthetic chemistry because alcohol is one of the most abundant raw chemicals. Specifically, direct coupling and deoxygenative coupling of alcohols are the two main approaches for the functionalization of alcohols to afford structurally diverse products, and it receives considerable attention. Despite significant advances in the field, there still remains a great challenge to develop a general approach accommodating both coupling reactions, as they commonly involve distinct pathways. Herein, we report an electrochemical approach for the direct coupling and deoxygenative coupling of alcohols with fluorenones. Under paired electrolysis, this catalyst-dependent protocol gives divergent access to diols and tertiary alcohols. Moreover, the synthetic utility of 9H-fluoren-9-ol products has been demonstrated in the synthesis of organic luminophores, phenanthrol, phenanthridine, and amino alcohol. The present approach exhibits some impressive features: (a) catalyst-dependent selectivity; (b) excellentfunctional-group tolerance (156 examples); (c) mild conditions; and (d) good scalability (∼20 gram scale).
AB - Developing a general and mild approach to upgrade alcohols into high value products is a hot topic in synthetic chemistry because alcohol is one of the most abundant raw chemicals. Specifically, direct coupling and deoxygenative coupling of alcohols are the two main approaches for the functionalization of alcohols to afford structurally diverse products, and it receives considerable attention. Despite significant advances in the field, there still remains a great challenge to develop a general approach accommodating both coupling reactions, as they commonly involve distinct pathways. Herein, we report an electrochemical approach for the direct coupling and deoxygenative coupling of alcohols with fluorenones. Under paired electrolysis, this catalyst-dependent protocol gives divergent access to diols and tertiary alcohols. Moreover, the synthetic utility of 9H-fluoren-9-ol products has been demonstrated in the synthesis of organic luminophores, phenanthrol, phenanthridine, and amino alcohol. The present approach exhibits some impressive features: (a) catalyst-dependent selectivity; (b) excellentfunctional-group tolerance (156 examples); (c) mild conditions; and (d) good scalability (∼20 gram scale).
KW - catalyst-dependent selectivity
KW - deoxygenative coupling
KW - direct coupling
KW - paired electrolysis
UR - http://www.scopus.com/inward/record.url?scp=85132327298&partnerID=8YFLogxK
U2 - 10.31635/ccschem.022.202101682
DO - 10.31635/ccschem.022.202101682
M3 - Article
AN - SCOPUS:85132327298
SN - 2096-5745
VL - 4
SP - 1938
EP - 1948
JO - CCS Chemistry
JF - CCS Chemistry
IS - 6
ER -