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my $filename = "/home/root/this_is_a_valid_name.html.gz";

if ($filename =~ m/(\.(htm|html|txt|pdf|ppt|csv|doc))$/i) {
    print "match\n"; # this won't print
}

my $filename = "/home/root/this_is_a_valid_name.html.gz";

if ($filename =~ /(\.(?:htm|html|txt|pdf|ppt|csv|doc]))\b/i) {
    print "match\n"; # this will print
}