c:\@Work\Perl\monks>perl -wMstrict -le
"use 5.010;
 ;;
 my $s =
   'Sent 1 12 to 1402, 222-2222, 1304, 555.555.5555 and 501, 666 666 6666 & 6789';
 print qq{'$s'};
 ;;
 my $sep = qr{ [-. ] }xms;
 my $pn  = qr{ \d{3} ($sep) (?: \d{3} \1)? \d{4} }xms;
 my $an  = qr{ \d{3,4} }xms;
 ;;
 $s =~ s{ (?| $pn (*SKIP)(*F) | (?<! \d) ($an) (?! \d)) }
        {<a $1><b>$1</b></a>}xmsg;
 print qq{'$s'};
"
'Sent 1 12 to 1402, 222-2222, 1304, 555.555.5555 and 501, 666 666 6666 & 6789'
'Sent 1 12 to <a 1402><b>1402</b></a>, 222-2222, <a 1304><b>1304</b></a>, 555.555.5555 and <a 501><b>501</b></a>, 666 666 6666 & <a 6789><b>6789</b></a>'