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Reaction of o ‐Carboryne with Furans: Facile Synthesis of Carborane‐ Fused Oxanorbornenes and Their Derivatives
Author(s) -
Zhang Rongyi,
Yuan Yinggen,
Qiu Zaozao,
Xie Zuowei
Publication year - 2018
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.201700772
Subject(s) - synthon , chemistry , carborane , halogenation , cycloaddition , nucleophile , ring (chemistry) , combinatorial chemistry , medicinal chemistry , organic chemistry , catalysis
o ‐Carboryne (1,2‐dehydro‐ o ‐carborane) is a very useful synthon for the synthesis of a variety of carborane‐functionalized molecules. Diels‐Alder reaction of o ‐carboryne with furans gave a series of carborane‐fused oxanorbornenes in moderate to high yields using 1‐OTf‐1,2‐C 2 B 10 H 11 as carboryne precursor. The resultant cycloadducts can undergo hydrogenation, cyclic oxidation, bromination, [4 + 2]/[2 + 2] cycloaddition and nucleophilic ring opening reaction to afford a variety of highly functionalized carboranes that may find applications as useful basic units in medicine and materials science.