No. Black can't cross the 3x3 gap.
There are many candidate moves so let us concentrate on more difficult ones - a keima, b kosumi and c attach.
is defeated by two clamping attachments,
and
. This line works for Black if the marked stone is missing (or results in a throw-in ko at
if the marked stone is at a).
tries a kind of "monkey jump on the second line", then White plays the attachment at
. Next, descending at
is key to prevent connection.
! prevents connection by keeping options on the third line open. After
, White pushes through the other side with
.
counter-clamp is an interesting try to make ko, but
and
separates the lower group even if Black wins the ko.
Related problems: Black needs some supporting stones to cross the 3x3 gap. See Xuanxuan Qijing Problem 132 and Gokyo Shumyo, Section 6, Problem 66.