Dearomative 1,6-addition of P(O)–H to in situ formed p-QM-like ion pairs from 2-benzofuryl-ols to C3-phosphinoyl hydrobenzofurans
Literature Information
Publication Date
2021-02-18
DOI
10.1039/D1QO00076D
Impact Factor
5.281
Authors
Long Chen, Yun-Xiang Zou, Shi-Lu Zheng, Xiao-Yan Liu, Hong-Li Yang, Jing Zhang, Yao Zeng, Li Duan, Zhong Wen, Hai-Liang Ni
View Original
Abstract
A dearomative C3-phosphorylation of 2-benzofuryl-ols with the P(O)–H species to C3-phosphinoyl hydrobenzofurans has been established. The key to achieve the high C3-regioselectivity is the use of an “OMe” group at the C6-position to enable the dearomative 1,6-addition of P(O)–H compounds to para-quinone methide (p-QM)-like ion pairs generated in situ from 2-benzofuran-ols. A “one-pot” tandem C3-phosphorylation/aromatization to C3-phosphinoyl benzofurans is also developed. This protocol not only provides an alternative method for the synthesis of C3-phosphinoyl hydrobenzofurans and benzofurans but also represents a new strategy for the dearomatization of benzofurans.
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Source Journal
Organic Chemistry Frontiers
CiteScore:
7.8
Self-citation Rate:
8.7%
Articles per Year:
724
Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry
Recommended Compounds
5,7-Dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-3-yl 2-O-(6-deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranoside
CAS Number:
32602-81-6
Molecular Formula:
C27H30O15
2-Chloro-4-nitrophenyl 6-deoxy-alpha-L-galactopyranoside
CAS Number:
157843-41-9
Molecular Formula:
C12H14ClNO7
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