Bis(aryl)acetal compounds
A bis(aryl)acetal has the formula wherein Y 1 and Y 2 are each independently chloro, bromo, iodo, mesylate, tosylate, triflate, or B x , provided that Y 1 and Y 2 are not both selected from chloro, bromo, and iodo; each occurrence of B x is independently a boron-containing functional group bonded to Ar 1 or Ar 2 via a boron atom; Ar 1 and Ar 2 are each independently unsubstituted or substituted C 6-18 arylene, or unsubstituted or substituted C 3-18 heteroarylene; provided that Ar 1 and Ar 2 are not covalently linked to each other to form a ring structure that includes —Ar 1 —O—C—O—Ar 2 —; and R 1 and R 2 are each independently hydrogen, unsubstituted or substituted C 1-18 linear or branched alkyl, unsubstituted or substituted C 3-20 cycloalkyl, unsubstituted or substituted C 6-18 aryl, or unsubstituted or substituted C 3-20 heteroaryl. The bis(aryl)acetal is useful as a monomer for oligoacetal and polyacetal synthesis via Suzuki polycondensation.
1. A bis(aryl)acetal having the formula
wherein
Y 1 and Y 2 are each independently chloro, bromo, iodo, mesylate, tosylate, triflate, or B x , provided that Y 1 and Y 2 are not both selected from chloro, bromo, and iodo;
each occurrence of B x is independently a boron-containing functional group bonded to Ar 1 or Ar 2 via a boron atom;
Ar 1 and Ar 2 are each independently unsubstituted or substituted C 6-18 arylene, or unsubstituted or substituted C 3-18 heteroarylene; provided that Ar 1 and Ar 2 are not covalently linked to each other to form a ring structure that includes
—Ar 1 —O—C—O—Ar 2 —; and
R 1 and R 2 are each independently hydrogen, unsubstituted or substituted C 1-18 linear or branched alkyl, unsubstituted or substituted C 3-20 cycloalkyl; unsubstituted or substituted C 6-18 aryl, or unsubstituted or substituted C 3-20 heteroaryl; and R 1 and R 2 are optionally covalently linked to each other to form a ring that includes
—R 1 —C—R 2 —.
2. The bis(aryl)acetal of claim 1 , wherein at least one of Y 1 and Y 2 is B x .
3. The bis(aryl)acetal of claim 1 , wherein Y 1 and Y 2 are each independently B x .
4. The bis(aryl)acetal of claim 1 , wherein each occurrence of B x is independently selected from the group consisting of —BF 3 − M + , wherein each occurrence of M + is independently an alkali metal cation, or an unsubstituted or substituted ammonium ion; —B(OH) 2 ;
wherein R 3 and R 4 are each independently C 1-18 alkyl, C 3-18 cycloalkyl, or C 6-18 aryl; and
R 3 and R 4 are optionally covalently linked to each other to form a ring that includes R 3 —O—B—O—R 4 ; and
wherein R 15 and R 16 are each independently hydrogen, unsubstituted or substituted C 1-18 linear or branched alkyl, unsubstituted or substituted C 3-18 cycloalkyl; unsubstituted or substituted C 6-18 aryl, unsubstituted or substituted C 3-18 heteroaryl, or
wherein Y 2 , Ar 1 , Ar 2 , R 1 , and R 2 are defined as in claim 1 .
5. The bis(aryl)acetal of claim 1 , wherein each occurrence of B x is
wherein R 3 and R 4 are each independently C 1-18 alkyl, C 3-18 cycloalkyl, or C 6-18 aryl; and
R 3 and R 4 are optionally covalently linked to each other to form a ring that includes R 3 —O—B—O—R 4 .
6. The bis(aryl)acetal of claim 1 , wherein Ar 1 and Ar 2 are each independently 1,3-phenylene or 1,4-phenylene.
7. The bis(aryl)acetal of claim 1 , wherein Ar 1 and Ar 2 are each independently 1,4-phenylene.
8. The bis(aryl)acetal of claim 1 , wherein
R 1 is hydrogen; and
R 2 is unsubstituted or substituted phenyl.
9. The bis(aryl)acetal of claim 1 , wherein
R 1 is hydrogen; and
R 2 is selected from phenyl, ortho-methoxyphenyl, meta-methoxyphenyl, and para-methoxyphenyl.
10. The bis(aryl)acetal of claim 1 , selected from the group consisting of